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Access for free at https://openstax.org/books/organic-chemistry/pages/1-why-this-chapter
- Authors: John McMurry, Professor Emeritus
- Publisher/website: OpenStax
- Book title: Organic Chemistry
- Publication date: Sep 20, 2023
- Location: Houston, Texas
- Book URL: https://openstax.org/books/organic-chemistry/pages/1-why-this-chapter
- Section URL: https://openstax.org/books/organic-chemistry/pages/chapter-10
© Jan 9, 2024 OpenStax. Textbook content produced by OpenStax is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike License . The OpenStax name, OpenStax logo, OpenStax book covers, OpenStax CNX name, and OpenStax CNX logo are not subject to the Creative Commons license and may not be reproduced without the prior and express written consent of Rice University.
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Chapter 10: Alkenes and Alkynes
![](http://2me.site/777/templates/cheerup/res/banner1.gif)
Answers to Chapter 10 Practice Questions
10.1 Show the structure of the major product for the following addition reactions.
![organic chemistry chapter 10 homework answers ""](https://kpu.pressbooks.pub/app/uploads/sites/139/2021/05/practice-answer-1-Ch-10.png)
10.2 For the addition of HBr to 3-methyl-1-butene, two products were observed. Show the reaction mechanism to explain the formation of both products.
![organic chemistry chapter 10 homework answers ""](https://kpu.pressbooks.pub/app/uploads/sites/139/2021/05/practice-question-2-Ch-10.png)
10.3 Show major product(s) for the following reactions.
![organic chemistry chapter 10 homework answers ""](https://kpu.pressbooks.pub/app/uploads/sites/139/2021/05/practice-answer-3-Ch-10.png)
10.4 Show major product(s) of the following reactions.
![organic chemistry chapter 10 homework answers ""](https://kpu.pressbooks.pub/app/uploads/sites/139/2021/05/practice-answer-4-Ch-10.png)
Organic Chemistry I Copyright © 2021 by Xin Liu is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License , except where otherwise noted.
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Answer Key 1-31
Problem 1-1
(a) 1 s 2 2 s 2 2 p 4
(b) 1 s 2 2 s 2 2 p 3
(c) 1 s 2 2 s 2 2 p 6 3 s 6 3 p 4
Problem 1-2
Problem 1-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image1-45.jpeg)
Problem 1-4
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image2-77.jpeg)
Problem 1-5
Problem 1-6
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image3-76.jpeg)
Problem 1-7
C2H7 has too many hydrogens for a compound with two carbons.
Problem 1-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image7-72.jpeg)
Problem 1-9
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image8-1.png)
Problem 1-10
The CH3 carbon is sp 3; the double-bond carbons are sp 2; the C=C−C and C=C−H bond angles are approximately 120°; other bond angles are near 109°.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image9-74.jpeg)
Problem 1-11
All carbons are sp 2, and all bond angles are near 120°.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image10-70.jpeg)
Problem 1-12
All carbons except CH3 are sp 2.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image11-71.jpeg)
Problem 1-13
The CH3 carbon is sp 3; the triple-bond carbons are sp; the C≡C−C and H−C≡C bond angles are approximately 180°.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image12-71.jpeg)
Problem 1-14
(a) O has 2 lone pairs and is sp 3-hybridized.
(b) N has 1 lone pair and is sp 3-hybridized.
(c) P has 1 lone pair and is sp 3-hybridized.
(d) S has 2 lone pairs and is sp 3-hybridized.
Problem 1-15
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image13-71.jpeg)
Problem 1-16
There are numerous possibilities, such as:
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image15-71.jpeg)
Problem 1-17
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image19-68.jpeg)
Problem 2-1
Problem 2-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image20-69.jpeg)
Problem 2-3
H3C−OH < H3C−MgBr < H3C−Li = H3C−F < H3C−K
Problem 2-4
The nitrogen is electron-rich, and the carbon is electron-poor.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image26-66.jpeg)
Problem 2-5
The two C–O dipoles cancel because of the symmetry of the molecule:
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image27-66.jpeg)
Problem 2-6
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image28-64.jpeg)
Problem 2-7
(a) For carbon: FC = 4 − 8/2 − 0 = 0 For the middle nitrogen: FC = 5 − 8/2 − 0 = +1 For the end nitrogen: FC = 5 − 4/2 − 4 = −1
(b) For nitrogen: FC = 5 − 8/2 − 0 = +1 For oxygen: FC = 6 − 2/2 − 6 = −1
(c) For nitrogen: FC = 5 − 8/2 − 0 = +1 For the triply bonded carbon: FC = 4 − 6/2 − 2 = −1
Problem 2-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image32-62.jpeg)
Problem 2-9
The structures in (a) are resonance forms.
Problem 2-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image33-61.jpeg)
Problem 2-11
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image37-59.jpeg)
Problem 2-12
Phenylalanine is stronger.
Problem 2-13
Water is a stronger acid.
Problem 2-14
Neither reaction will take place.
Problem 2-15
Reaction will take place.
Problem 2-16
K a = 4.9 × 10–10
Problem 2-17
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image38-57.jpeg)
Problem 2-18
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image40-56.jpeg)
Problem 2-19
Vitamin C is water-soluble (hydrophilic); vitamin A is fat-soluble (hydrophilic).
Problem 3-1
(a) Sulfide, carboxylic acid, amine
(b) Aromatic ring, carboxylic acid
(c) Ether, alcohol, aromatic ring, amide, C=C bond
Problem 3-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image42-1.png)
Problem 3-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image48-57.jpeg)
Problem 3-4
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image49-57.jpeg)
Problem 3-5
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image50-54.jpeg)
Problem 3-6
(a) Two (b) Four (c) Four
Problem 3-7
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image53-53.jpeg)
Problem 3-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image54-52.jpeg)
Problem 3-9
Primary carbons have primary hydrogens, secondary carbons have secondary hydrogens, and tertiary carbons have tertiary hydrogens.
Problem 3-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image57-52.jpeg)
Problem 3-11
(a) Pentane, 2-methylbutane, 2,2-dimethylpropane
(b) 2,3-Dimethylpentane
(c) 2,4-Dimethylpentane
(d) 2,2,5-Trimethylhexane
Problem 3-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image60-47.jpeg)
Problem 3-13
Pentyl, 1-methylbutyl, 1-ethylpropyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl
Problem 3-14
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image64-44.jpeg)
Problem 3-15
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image65-44.jpeg)
Problem 3-16
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image66-45.jpeg)
Problem 3-17
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image69-44.jpeg)
Problem 3-18
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image70-41.jpeg)
Problem 4-1
(a) 1,4-Dimethylcyclohexane
(b) 1-Methyl-3-propylcyclopentane
(c) 3-Cyclobutylpentane
(d) 1-Bromo-4-ethylcyclodecane
(e) 1-Isopropyl-2-methylcyclohexane
(f) 4-Bromo-1- tert -butyl-2-methylcycloheptane
Problem 4-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image71-41.jpeg)
Problem 4-3
3-Ethyl-1,1-dimethylcyclopentane
Problem 4-4
(a) trans -1-Chloro-4-methylcyclohexane (b) cis -1-Ethyl-3-methylcycloheptane
Problem 4-5
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image75-39.jpeg)
Problem 4-6
The two hydroxyl groups are cis. The two side chains are trans.
Problem 4-7
(a) cis -1,2-Dimethylcyclopentane
(b) cis -1-Bromo-3-methylcyclobutane
Problem 4-8
Six interactions; 21% of strain
Problem 4-9
The cis isomer is less stable because the methyl groups nearly eclipse each other.
Problem 4-10
Ten eclipsing interactions; 40 kJ/mol; 35% is relieved.
Problem 4-11
Conformation (a) is more stable because the methyl groups are farther apart.
Problem 4-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image78-37.jpeg)
Problem 4-13
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image79-37.jpeg)
Problem 4-14
Before the ring-flip, red and blue are equatorial and green is axial. After the ring-flip, red and blue are axial and green is equatorial.
Problem 4-15
Problem 4-16
Cyano group points straight up.
Problem 4-17
Equatorial = 70%; axial = 30%
Problem 4-18
(a) 2.0 kJ/mol (axial Cl)
(b)11.4 kJ/mol (axial CH3)
(c) 2.0 kJ/mol (axial Br)
(d) 8.0 kJ/mol (axial CH2CH3)
Problem 4-19
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image80-36.jpeg)
Problem 4-20
trans -Decalin is more stable because it has no 1,3-diaxial interactions.
Problem 4-21
Both ring-fusions are trans.
Problem 5-1 Chiral: screw, shoe Problem 5-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image81-35.jpeg)
Problem 5-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image84-34.jpeg)
Problem 5-4 (a)
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image85-35.jpeg)
Problem 5-5 Levorotatory Problem 5-6
Problem 5-7 (a)
Problem 5-8 (a)
−OH, −CH2CH2OH, −CH2CH3, −H
−OH, −CO2CH3, −CO2H, −CH2OH
−NH2, −CN, −CH2NHCH3, −CH2NH2
−SSCH3, −SH, −CH2SCH3, −CH3
Problem 5-9 (a)
Problem 5-10 (a)
Problem 5-11
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image87-34.jpeg)
Problem 5-12
Problem 5-13
Compound (a) is D-erythrose 4-phosphate, (d) is its enantiomer, and (b) and (c) are diastereomers.
Problem 5-14
Five chirality centers and 25 = 32 stereoisomers Problem 5-15
Problem 5-16
Compounds (a) and (d) are meso. Problem 5-17
Compounds (a) and (c) have meso forms.
Problem 5-18
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image88-34.jpeg)
Problem 5-20
Two diastereomeric salts: ( R )-lactic acid plus ( S )-1-phenylethylamine and ( S )-lactic acid plus ( S )-1-phenylethylamine
Problem 5-21 (a)
Constitutional isomers (b)
Diastereomers Problem 5-22 (a)
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image89-34.jpeg)
Problem 5-23 (a)
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image91-32.jpeg)
Problem 5-24 ( S )-Lactate Problem 5-25
The −OH adds to the Re face of C2, and −H adds to the Re face of C3. The overall addition has anti stereochemistry.
Problem 6-1
(a) Substitution (b) Elimination (c) Addition
Problem 6-2
(a) Carbon is electrophilic.
(b) Sulfur is nucleophilic.
(c) Nitrogens are nucleophilic.
(d) Oxygen is nucleophilic; carbon is electrophilic.
Problem 6-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image93-31.jpeg)
Problem 6-4
Bromocyclohexane; chlorocyclohexane
Problem 6-5
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image94-29.jpeg)
The mechanism is shown in Figure 6.4
Problem 6-6
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image95-29.jpeg)
Problem 6-7
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image98-29.jpeg)
Problem 6-8
1-Chloro-2-methylpentane, 2-chloro-2-methylpentane, 3-chloro-2-methylpentane, 2- chloro-4-methylpentane, 1-chloro- 4-methylpentane
Problem 6-9
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image99-29.jpeg)
Problem 6-10
Negative Δ G ° is favored.
Problem 6-11
Larger K eq is more exergonic.
Problem 6-12
Lower Δ G ‡ is faster.
Problem 6-13
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image100-30.jpeg)
Problem 7-1
Problem 7-2
Problem 7-3
C16H13ClN2O
Problem 7-4
(a) 3,4,4-Trimethyl-1-pentene
(b)3-Methyl-3-hexene
(c) 4,7-Dimethyl-2,5-octadiene
(d) 6-Ethyl-7-methyl-4-nonene
Problem 7-5
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image101-29.jpeg)
Problem 7-6
(a) 1,2-Dimethylcyclohexene
(b) 4,4-Dimethylcycloheptene
(c) 3-Isopropylcyclopentene
Problem 7-7
(a) 2,5,5-Trimethylhex-2-ene
(b) 2,3-Dimethylcyclohexa-1,3-diene
Problem 7-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image105-29.jpeg)
Problem 7-9
Compounds (c) , (e) , and (f) have cis–trans isomers.
Problem 7-10
(a) cis -4,5-Dimethyl-2-hexene
(b) trans -6-Methyl-3-heptene
Problem 7-11
(c) −CH=CH2
Problem 7-12
(a) −Cl, −OH, −CH3, −H
(b) −CH2OH, −CH=CH2, −CH2CH3, −CH3
(c) −CO2H, −CH2OH, −C≡N, −CH2NH2
(d) −CH2OCH3, −C≡N, −C≡CH, −CH2CH3
Problem 7-13
Problem 7-14
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image106-29.jpeg)
Problem 7-15
(a)2-Methylpropene is more stable than 1-butene.
(b) trans -2-Hexene is more stable than cis -2-hexene.
(c) Methylcyclohexene is more stable than 3-methylcyclohexene.
Problem 7-16
(a) Chlorocyclohexane
(b) Bromo-2-methylpentane
(c) 4-Methyl-2-pentanol
(d) 1-Bromo-1-methylcyclohexane
Problem 7-17
(a) Cyclopentene
(b) 1-Ethylcyclohexene or ethylidenecyclohexane
(c) 3-Hexene
(d) Vinylcyclohexane (cyclohexylethylene)
Problem 7-18
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image107-26.jpeg)
Problem 7-19
In the conformation shown, only the methyl- group C−H that is parallel to the carbocation p orbital can show hyperconjugation.
Problem 7-20
The second step is exergonic; the transition state resembles the carbocation.
Problem 7-21
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image109-26.jpeg)
Problem 8-1
2-Methyl-2-butene and 2-methyl-1-butene
Problem 8-2
Problem 8-3
trans -1,2-Dichloro-1,2-dimethylcyclohexane
Problem 8-4
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image110-26.jpeg)
Problem 8-5
trans -2-Bromocyclopentanol
Problem 8-6
Markovnikov
Problem 8-7
(a) 2-Pentanol (b) Methyl-2-pentanol
Problem 8-8
(a) Oxymercuration of 2-methyl-1-hexene or 2-methyl-2-hexene
(b) Oxymercuration of cyclohexylethylene or hydroboration of ethylidenecyclohexane
Problem 8-9
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image111-26.jpeg)
Problem 8-10
(a) Methyl-1-butene (b) 2-Methyl-2-butene (c) Methylenecyclohexane
Problem 8-11
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image113-26.jpeg)
Problem 8-12 (a) 2-Methylpentane (b) 1,1-Dimethylcyclopentane (c) tert -Butylcyclohexane
Problem 8-13
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image114-26.jpeg)
Problem 8-14
(a) Methylcyclohexene
(b) Methyl-2-pentene
(c) 1,3-Butadiene
Problem 8-15
(a) CH3COCH2CH2CH2CH2CO2H
(b) CH3COCH2CH2CH2CH2CHO
Problem 8-16
(a) Methylpropene
Problem 8-17
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image115-26.jpeg)
Problem 8-18
(a) H2C═CHOCH3
(b) ClCH═CHCl
Problem 8-19
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image117-24.jpeg)
Problem 8-20
An optically inactive, non-50 : 50 mixture of two racemic pairs: (2 R ,4 R ) + (2 S ,4 S ) and (2 R ,4 S ) + (2 S ,4 R )
Problem 8-21
Non-50 : 50 mixture of two racemic pairs: (1 S ,3 R ) + (1 R ,3 S ) and (1 S ,3 S ) + (1 R ,3 R )
Problem 9-1
(a) 2,5-Dimethyl-3-hexyne
(b) 3,3-Dimethyl-1-butyne (
c) 3,3-Dimethyl-4-octyne
(d) 2,5,5-Trimethyl-3-heptyne
(e) 2,4-Octadiene-6-yne
Problem 9-2
1-Hexyne, 2-hexyne, 3-hexyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 4-methyl-2- pentyne, 3,3-dimethyl-1-butyne
Problem 9-3
(a) 1,1,2,2-Tetrachloropentane
(b) Bromo-1-cyclopentylethylene
(c) Bromo-2-heptene and 3-bromo-2-heptene
Problem 9-4
(a) 4-Octanone
(b) 2-Methyl-4-octanone and 7-methyl-4-octanone
Problem 9-5
(a) Pentyne
(b) Pentyne
Problem 9-6
(a) C6H5C≡CH
(b) 2,5-Dimethyl-3-hexyne
Problem 9-7
(a) Mercuric sulfate–catalyzed hydration of phenylacetylene
(b) Hydroboration/oxidation of cyclopentylacetylene
Problem 9-8
(a) Reduce 2-octyne with Li/NH3.
(b) Reduce 3-heptyne with H2/Lindlar catalyst.
(c) Reduce 3-methyl-1-pentyne.
Problem 9-9
No: (a) , (c) , (d) ; yes: (b)
Problem 9-10
(a) 1-Pentyne + CH3I, or propyne + CH3CH2CH2I
(b) 3-Methyl-1-butyne + CH3CH2I
(c) Cyclohexylacetylene + CH3I Problem 9-11
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image118-24.jpeg)
Problem 9-12
(a) KMnO4, H3O+
(b) H2/Lindlar
(c) 1. H2/Lindlar; 2. HBr
(d) 1. H2/Lindlar; 2. BH3; 3. NaOH, H2O2
(e) 1. H2/Lindlar; 2. Cl2
Problem 9-13
(a) 1. HC≡CH + NaNH2 ; 2. CH3(CH2)6CH2Br; 3. 2 H2/Pd
(b) HC≡CH + NaNH2 ; 2. (CH3)3CCH2CH2I; 3. 2 H2/Pd
(c) 1. HC≡CH + NaNH2 ; 2. CH3CH2CH2CH2I; 3. BH3; 4. H2O2
(d) 1. HC≡CH + NaNH2 ; 2. CH3CH2CH2CH2CH2I; 3. HgSO4, H3O+
Problem 10-1
(a) 1-Iodobutane
(b) 1-Chloro-3-methylbutane
(c) 1,5-Dibromo-2,2-dimethylpentane
(d) 1,3-Dichloro-3-methylbutane
(e) Chloro-3-ethyl-4-iodopentane
(f) Bromo-5-chlorohexane
Problem 10-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image119-26.jpeg)
Problem 10-3
Chiral: 1-chloro-2-methylpentane, 3-chloro-2-methylpentane, 2-chloro-4-methylpentane Achiral: 2-chloro-2-methylpentane, 1-chloro-4-methylpentane
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image125-23.jpeg)
Problem 10-4
1-Chloro-2-methylbutane (29%), 1-chloro-3-methylbutane (14%), 2-chloro-2-
methylbutane (24%), 2-chloro-3-methylbutane (33%)
Problem 10-5
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image133-23.jpeg)
Problem 10-6
The intermediate allylic radical reacts at the more accessible site and gives the more highly substituted double bond.
Problem 10-7
(a) 3-Bromo-5-methylcycloheptene and 3-bromo-6-methylcycloheptene
(b)Four products
Problem 10-8
(a) 2-Methyl-2-propanol + HCl
(b) 4-Methyl-2-pentanol + PBr3
(c) 5-Methyl-1-pentanol + PBr3
(d) 3,3-Dimethyl-cyclopentanol + HF, pyridine
Problem 10-9
Both reactions occur.
Problem 10-10
React Grignard reagent with D2O.
Problem 10-11
(a) 1. NBS; 2. (CH3)2CuLi
(b) 1. Li; 2. CuI; 3. CH3CH2CH2CH2Br
(c) 1. BH3; 2. H2O2, NaOH; 3. PBr3; 4. Li, then CuI; 5. CH3(CH2)4Br
Problem 10-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image134-23.jpeg)
Problem 10-13
(a) Reduction (b) Neither
Problem 11-1
( R )-1-Methylpentyl acetate, CH3CO2CH(CH3)CH2CH2CH2CH3
Problem 11-2
( S )-2-Butanol
Problem 11-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image136-21.jpeg)
Problem 11-4
(b) 1-Butanol
(c) 1-Hexyne
(d) Butylammonium bromide
Problem 11-5
(a) (CH3)2N−
(b) (CH3)3N
Problem 11-6
CH3OTos > CH3Br > (CH3)2CHCl > (CH3)3CCl
Problem 11-7
Similar to protic solvents
Problem 11-8
Racemic 1-ethyl-1-methylhexyl acetate
Problem 11-9
90.1% racemization, 9.9% inversion
Problem 11-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image137-21.jpeg)
Problem 11-11
H2C═CHCH(Br)CH3 > CH3CH(Br)CH3 > CH3CH2Br > H2C═CHBr
Problem 11-12
The same allylic carbocation intermediate is formed.
Problem 11-13
Problem 11-14
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image138-20.jpeg)
Problem 11-15
(a) Major: 2-methyl-2-pentene; minor: 4-methyl-2-pentene
(b) Major: 2,3,5-trimethyl-2-hexene; minor: 2,3,5-trimethyl-3-hexene and 2-isopropyl-4- methyl-1-pentene
(c) Major: ethylidenecyclohexane; minor: cyclohexylethylene
Problem 11-16
(a) 1-Bromo-3,6-dimethylheptane (b) 4-Bromo-1,2-dimethylcyclopentane
Problem 11-17
( Z )-1-Bromo-1,2-diphenylethylene
Problem 11-18
( Z )-3-Methyl-2-pentene
Problem 11-19
Cis isomer reacts faster because the bromine is axial.
Problem 11-20
(a) SN2 (b) E2 (c) SN1 (d) E1cB
Problem 12-1
Problem 12-2
(a) 2-Methyl-2-pentene (b) 2-Hexene
Problem 12-3
Problem 12-4
102 (M+), 84 (dehydration), 87 (alpha cleavage), 59 (alpha cleavage)
Problem 12-5
X-ray energy is higher; λ = 9.0 × 10−6 m is higher in energy.
Problem 12-6
(a) 2.4 × 106 kJ/mol] (b) 4.0 × 104 kJ/mol (c) 2.4 × 103 kJ/mol (d) 2.8 × 102 kJ/mol (e) 6.0 kJ/mol (f) 4.0 × 10−2 kJ/mol
Problem 12-7
(a) Ketone or aldehyde (b) Nitro compound (c) Carboxylic acid
Problem 12-8
(a) CH3CH2OH has an −OH absorption. (b) 1-Hexene has a double-bond absorption. (c) CH3CH2CO2H has a very broad −OH absorption.
Problem 12-9
1450–1600 cm−1: aromatic ring; 2100 cm−1: C≡C; 3300 cm−1: C≡C−H
Problem 12-10
(a) 1715, 1640, 1250 cm−1
(b) 1730, 2100, 3300 cm−1
(c) 1720, 2500–3100, 3400–3650 cm−1
Problem 12-11
1690, 1650, 2230 cm−1
Problem 13-1
7.5 × 10−5 kJ/mol for 19F; 8.0 × 10−5 kJ/mol for 1H
Problem 13-2
1.2 × 10−4 kJ/mol
Problem 13-3
The vinylic C − H protons are nonequivalent.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image139-20.jpeg)
Problem 13-4
Problem 13-5 (a) 420 Hz (b) 2.1 δ (c) 1050 Hz
Problem 13-6
(a) 1.43 δ (b) 2.17 δ (c) 7.37 δ (d) 5.30 δ (e) 9.70 δ (f) 2.12 δ
Problem 13-7
There are seven kinds of protons labeled. The types and expected range of absorption of each follow. a: ether, 3.5–4.5 δ ; b: aryl, 6.5–8.0 δ ; c: aryl, 6.5–8.0; d: vinylic, 4.5–6.5 δ ; e: vinylic, 4.5–6.5 δ ; f: alkyl (secondary), 1.2–1.6 δ ; g: alkyl (primary), 0.7–1.3 δ .
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image140-21.jpeg)
Problem 13-8
Two peaks; 3 : 2 ratio
Problem 13-9
(a) −CHBr2, quartet; −CH3, doublet (b) CH3O−, singlet; −OCH2 −, triplet; −CH2Br, triplet (c) ClCH2− , triplet; −CH2−, quintet (d) CH3− , triplet; −CH2− , quartet; −CH− , septet; (CH3)2, doublet (e) CH3−, triplet; −CH2−, quartet; −CH−, septet; (CH3)2, doublet (f) =CH, triplet, −CH2−, doublet, aromatic C−H, two multiplets
Problem 13-10
(a) CH3OCH3
(b) CH3CH(Cl)CH3
(c) ClCH2CH2OCH2CH2Cl
(d) CH3CH2CO2CH3 or CH3CO2CH2CH3
Problem 13-11
CH3CH2OCH2CH3
Problem 13-12 (a) Enantiotopic (b) Diastereotopic (c) Diastereotopic (d) Diastereotopic (e) Diastereotopic (f) Homotopic
Problem 13-13
Problem 13-14
Problem 13-15
J 1–2 = 16 Hz; J 2–3 = 8 Hz
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image141-21.jpeg)
Problem 13-16
Chloro-1-methylcyclohexane has a singlet methyl absorption.
Problem 13-17
Problem 13-18
(a) 1,3-Dimethylcyclopentene (b) Methylpentane (c) 1-Chloro-2-methylpropane
Problem 13-19
−CH3, 9.3 δ; −CH2− , 27.6 δ; C=O, 174.6 δ; − OCH3, 51.4 δ
Problem 13-20
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image142-21.jpeg)
Problem 13-21
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image143-21.jpeg)
Problem 13-22
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image144-21.jpeg)
Problem 13-23
A DEPT-90 spectrum would show two absorptions for the non-Markovnikov product (RCH=CHBr) but no absorptions for the Markovnikov product (RBrC=CH2).
Problem 14-1
Expected Δ H °hydrog for allene is −252 kJ/mol. Allene is less stable than a nonconjugated diene, which is less stable than a conjugated diene.
Problem 14-2
1-Chloro-2-pentene, 3-chloro-1-pentene, 4-chloro-2-pentene
Problem 14-3
4-Chloro-2-pentene predominates in both.
Problem 14-4
1,2 Addition: 6-bromo-1,6-dimethylcyclohexene 1,4 Addition: 3-bromo-1,2- dimethylcyclohexene
Problem 14-5
Interconversion occurs by SN1 dissociation to a common intermediate cation.
Problem 14-6
The double bond is more highly substituted.
Problem 14-7
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image145-21.jpeg)
Problem 14-8
Good dienophiles: (a) , (d)
Problem 14-9
Compound (a) is s -cis. Compound (c) can rotate to s -cis.
Problem 14-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image146-20.jpeg)
Problem 14-11
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image147-20.jpeg)
Problem 14-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image148-15.jpeg)
Problem 14-13
300–600 kJ/mol; UV energy is greater than IR or NMR energy.
Problem 14-14
1.46 × 10−5 M
Problem 14-15
All except (a) have UV absorptions.
Problem 15-1
(a) Meta (b) Para (c) Ortho
Problem 15-2
(a) m -Bromochlorobenzene (b) (3-Methylbutyl)benzene (c) p -Bromoaniline (d) 2,5-Dichlorotoluene (e) 1-Ethyl-2,4-dinitrobenzene (f) 1,2,3,5-Tetramethylbenzene
Problem 15-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image149-19.jpeg)
Problem 15-4
Pyridine has an aromatic sextet of electrons.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image153-17.jpeg)
Problem 15-5
Cyclodecapentaene is not flat because of steric interactions.
Problem 15-6
All C–C bonds are equivalent; one resonance line in both 1H and 13C NMR spectra.
Problem 15-7
The cyclooctatetraenyl dianion is aromatic (ten π electrons) and flat.
Problem 15-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image154-17.jpeg)
Problem 15-9
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image155-18.jpeg)
Problem 15-10
The thiazolium ring has six π electrons.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image156-17.jpeg)
Problem 15-11 Yes, it’s aromatic.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image157-17.jpeg)
Problem 15-12
The three nitrogens in double bonds each contribute one; the remaining nitrogen contributes two.
Problem 16-1
o-, m-, and p-Bromotoluene
Problem 16-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image158-17.jpeg)
Problem 16-3
o -xylene: 2; p -xylene: 1; m -xylene: 3
Problem 16-4
D+ does electrophilic substitutions on the ring.
Problem 16-5
No rearrangement: (a), (b), (e)
Problem 16-6
tert -Butylbenzene
Problem 16-7
(a) (CH3)2CHCOCl
Problem 16-8
(a)Phenol > Toluene > Benzene > Nitrobenzene
(b)Phenol > Benzene > Chlorobenzene > Benzoic acid
(c) Aniline > Benzene > Bromobenzene > Benzaldehyde
Problem 16-9
(a) o – and p -Bromonitrobenzene (b) m -Bromonitrobenzene (c) o – and p -Chlorophenol (d) o – and p -Bromoaniline
Problem 16-10
Alkylbenzenes are more reactive than benzene itself, but acylbenzenes are less reactive.
Problem 16-11
Toluene is more reactive; the trifluoromethyl group is electron-withdrawing.
Problem 16-12
The nitrogen electrons are donated to the nearby carbonyl group by resonance and are less available to the ring.
Problem 16-13
The meta intermediate is most favored.
Problem 16-14
(a) Ortho and para to −OCH3 (b) Ortho and para to −NH2 (c) Ortho and para to −Cl
Problem 16-15
(a) Reaction occurs ortho and para to the −CH3 group.
(b) Reaction occurs ortho and para to the −OCH3 group.
Problem 16-16
The phenol is deprotonated by KOH to give an anion that carries out a nucleophilic acyl substitution reaction on the fluoronitrobenzene.
Problem 16-17
Only one benzyne intermediate can form from p -bromotoluene; two different benzyne intermediates can form from m -bromotoluene.
Problem 16-18
(a) m -Nitrobenzoic acid (b) p – tert -Butylbenzoic acid
Problem 16-19
A benzyl radical is more stable than a primary alkyl radical by 52 kJ/mol and is similar in stability to an allyl radical.
Problem 16-20
1. CH3CH2Cl, AlCl3; 2. NBS; 3. KOH, ethanol
Problem 16-21
1. PhCOCl, AlCl3; 2. H2/Pd
Problem 16-22
(a) 1. HNO3, H2SO4; 2. Cl2, FeCl3
(b) 1. CH3COCl, AlCl3; 2. Cl2, FeCl3; 3. H2/Pd
(c) 1. CH3CH2COCl, AlCl3; 2. Cl2, FeCl3; 3. H2/Pd; 4. HNO3, H2SO4
(d) 1. CH3Cl, AlCl3; 2. Br2, FeBr3; 3. SO3, H2SO4
Problem 16-23
(a) Friedel–Crafts acylation does not occur on a deactivated ring.
(b) Rearrangement occurs during Friedel–Crafts alkylation with primary halides; chlorination occurs ortho to the alkyl group.
Problem 17-1
(a) 5-Methyl-2,4-hexanediol (b) 2-Methyl-4-phenyl-2-butanol (c) 4,4-Dimethylcyclohexanol (d) trans -2-Bromocyclopentanol (e) 4-Bromo-3-methylphenol (f) 2-Cyclopenten-1-ol
Problem 17-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image159-17.jpeg)
Problem 17-3
Hydrogen-bonding is more difficult in hindered alcohols.
Problem 17-4
(a) HC≡CH < (CH3)2CHOH < CH3OH < (CF3)2CHOH
(b) p -Methylphenol < Phenol < p -(Trifluoromethyl)phenol
(c) Benzyl alcohol < Phenol < p -Hydroxybenzoic acid
Problem 17-5
The electron-withdrawing nitro group stabilizes an alkoxide ion, but the electron-donating methoxyl group destabilizes the anion.
Problem 17-6
(a) 2-Methyl-3-pentanol
(b) 2-Methyl-4-phenyl-2-butanol
(c) meso -5,6-Decanediol
Problem 17-7
Problem 17-8
(a) Benzaldehyde or benzoic acid (or ester)
(b) Acetophenone
(c) Cyclohexanone
(d) 2-Methylpropanal or 2-methylpropanoic acid (or ester)
Problem 17-9
(a) 1-Methylcyclopentanol (b) 1,1-Diphenylethanol (c) 3-Methyl-3-hexanol
Problem 17-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image165-13.jpeg)
Problem 17-11
Cyclohexanone + CH3CH2MgBr
Problem 17-12
1. p -TosCl, pyridine; 2. NaCN
Problem 17-13
(a) Methyl-2-pentene (b) Methylcyclohexene (c) Methylcyclohexene (d) 2,3-Dimethyl-2-pentene (e) Methyl-2-pentene
Problem 17-14
(a) Phenylethanol (b) Methyl-1-propanol (c) Cyclopentanol
Problem 17-15
(a) Hexanoic acid, hexanal
(b) 2-Hexanone
(c) Hexanoic acid, no reaction
Problem 17-16
SN2 reaction of F− on silicon with displacement of alkoxide ion.
Problem 17-17
Protonation of 2-methylpropene gives the tert -butyl cation, which carries out an electrophilic aromatic substitution reaction.
Problem 17-18
Disappearance of –OH absorption; appearance of C=O
Problem 17-19
(a) Singlet (b) Doublet (c) Triplet (d) Doublet (e) Doublet (f) Singlet
Problem 18-1
(a) Diisopropyl ether (b) Cyclopentyl propyl ether (c p -Bromoanisole or 4-bromo-1-methoxybenzene (d) Methoxycyclohexene (e) Ethyl isobutyl ether (f Allyl vinyl ether
Problem 18-2
A mixture of diethyl ether, dipropyl ether, and ethyl propyl ether is formed in a 1 : 1 : 2 ratio.
Problem 18-3
(a) CH3CH2CH2O− + CH3Br
(b) PhO− + CH3Br
(c) (CH3)2CHO− + PhCH2Br
(d) (CH3)3CCH2O− + CH3CH2Br
Problem 18-4
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image171-12.jpeg)
Problem 18-5
(a) Either method (b) Williamson (c) Alkoxymercuration (d) Williamson
Problem 18-6
(a) Bromoethane > 2-Bromopropane > Bromobenzene
(b) Bromoethane > Chloroethane > 1-Iodopropene
Problem 18-7
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image172-12.jpeg)
Problem 18-8
Protonation of the oxygen atom, followed by E1 reaction
Problem 18-9
Br− and I− are better nucleophiles than Cl−.
Problem 18-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image174-12.jpeg)
Problem 18-11
Epoxidation of cis -2-butene yields cis -2,3-epoxybutane, while epoxidation of trans -2- butene yields trans -2,3-epoxybutane.
Problem 18-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image175-11.jpeg)
Problem 18-13
(a) 1-Methylcyclohexene + OsO4; then NaHSO3
(b) 1-Methylcyclohexene + m -chloroperoxybenzoic acid, then H3O+
Problem 18-14
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image177-11.jpeg)
Problem 18-15
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image180-11.jpeg)
Problem 18-16
(a) Butanethiol (b) 2,2,6-Trimethyl-4-heptanethiol (c) 2-Cyclopentene-1-thiol (d) Ethyl isopropyl sulfide (e) Di(methylthio)benzene (f) 3-(Ethylthio)cyclohexanone
Problem 18-17
(a) 1. LiAlH4; 2. PBr3; 3. (𝐻 ! 𝑁)!𝐶═𝑆; 4. H2O, NaOH
(b) 1. HBr; 2. (𝐻 ! 𝑁)!𝐶═𝑆; 3. H2O, NaOH
Problem 18-18
1,2-Epoxybutane
Problem 18-69
Acetyl chloride is more electrophilic than acetone.
Problem 18-70
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image181-11.jpeg)
Problem 18-71
(a) Nucleophilic acyl substitution (b) Nucleophilic addition (c) Carbonyl condensation
Problem 19-1
(a) Methyl-3-pentanone (b) Phenylpropanal (c) 2,6-Octanedione (d) trans -2-Methylcyclohexanecarbaldehyde (e) Hexenal (f) cis -2,5-Dimethylcyclohexanone
Problem 19-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image182-11.jpeg)
Problem 19-3
(a) Dess–Martin periodinane (b) 1. O3; 2. Zn (c) DIBAH (d) 1. BH3, then H2O2, NaOH; 2. Dess–Martin periodinane
Problem 19-4
(a) HgSO4, H3O+
(b) 1. CH3COCl, AlCl3; 2. Br2, FeBr3
(c) 1. Mg; 2. CH3CHO; 3. H3O+; 4. CrO3
(d) 1. BH3; 2. H2O2, NaOH; 3. CrO3
Problem 19-5
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image188-11.jpeg)
Problem 19-6
The electron-withdrawing nitro group in p -nitrobenzaldehyde polarizes the carbonyl group.
Problem 19-7
CCl3CH(OH)2
Problem 19-8
Labeled water adds reversibly to the carbonyl group.
Problem 19-9
The equilibrium is unfavorable for sterically hindered ketones.
Problem 19-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image189-10.jpeg)
Problem 19-11
The steps are the exact reverse of the forward reaction shown in Figure 19.7.
Problem 19-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image190-9.jpeg)
Problem 19-13
(a) H2/Pd (b) N2H4, KOH (c) 1. H2/Pd; 2. N2H4, KOH
Problem 19-14
The mechanism is identical to that between a ketone and 2 equivalents of a monoalcohol, shown in Figure 19.11.
Problem 19-15
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image191-8.jpeg)
Problem 19-16
(a) Cyclohexanone + (Ph)3P=CHCH3
(b) Cyclohexanecarbaldehyde + (Ph)3P=CH2
(c) Acetone + (Ph)3P=CHCH2CH2CH3
(d) Acetone + (Ph)3P=CHPh
(e) PhCOCH3 + (Ph)3P=CHPh
(f) 2-Cyclohexenone + (Ph)3P=CH2
Problem 19-17
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image192-8.jpeg)
Problem 19-18
Intramolecular Cannizzaro reaction
Problem 19-19
Addition of the pro- R hydrogen of NADH takes place on the Re face of pyruvate.
Problem 19-20
The −OH group adds to the Re face at C2, and −H adds to the Re face at C3, to yield (2 R ,3 S )- isocitrate.
Problem 19-21
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image193-8.jpeg)
Problem 19-22
(a) 3-Buten-2-one + (CH3CH2CH2)2CuLi (b) 3-Methyl-2-cyclohexenone + (CH3)2CuLi (c) 4- tert -Butyl-2-cyclohexenone + (CH3CH2)2CuLi (d) Unsaturated ketone + (H2C=CH)2CuLi
Problem 19-23
Look for appearance of either an alcohol or a saturated ketone in the product.
Problem 19-24
(a) 1715 cm−1
(b) 1685 cm−1
(c) 1750 cm−1
(d) 1705 cm−1
(e) 1715 cm−1
(f) 1705 cm−1
Problem 19-25
(a) Different peaks due to McLafferty rearrangement
(b) Different peaks due to α cleavage and McLafferty rearrangement
(c) Different peaks due to McLafferty rearrangement
Problem 19-26
IR: 1750 cm−1; MS: 140, 84
Problem 20-1
(a)Methylbutanoic acid (b) Bromopentanoic acid (c) 2-Ethylpentanoic acid (d) cis -4-Hexenoic acid (e) 2,4-Dimethylpentanenitrile (f) cis -1,3-Cyclopentanedicarboxylic acid
Problem 20-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image194-9.jpeg)
Problem 20-3
Dissolve the mixture in ether, extract with aqueous NaOH, separate and acidify the aqueous layer, and extract with ether.
Problem 20-4
Problem 20-5
(a) 82% dissociation (b) 73% dissociation
Problem 20-6
Lactic acid is stronger because of the inductive effect of the −OH group.
Problem 20-7
The dianion is destabilized by repulsion between charges.
Problem 20-8
More reactive
Problem 20-9
(a) p -Methylbenzoic acid < Benzoic acid < p -Chlorobenzoic acid
(b) Acetic acid < Benzoic acid < p -Nitrobenzoic acid
Problem 20-10
(a) 1. Mg; 2. CO2; 3. H3O+
(b) 1. Mg; 2. CO2; 3. H3O+ or 1. NaCN; 2. H3O+
Problem 20-11
1. NaCN; 2. H3O+; 3. LiAlH4
Problem 20-12
1. PBr3; 2. NaCN; 3. H3O+; 4. LiAlH4
Problem 20-13
(a) Propanenitrile + CH3CH2MgBr, then H3O+ (b) p -Chlorobenzonitrile + CH3MgBr, then H3O+
Problem 20-14
1. NaCN; 2. CH3CH2MgBr, then H3O+
Problem 20-15
A carboxylic acid has a very broad −OH absorption at 2500–3300 cm−1.
Problem 20-16
4-Hydroxycyclohexanone: H–C–O absorption near 4 δ in the 1H spectrum and C═O absorption near 210 δ in the 13C spectrum. Cyclopentanecarboxylic acid: –CO2H absorption near 12 δ in the 1H spectrum and –CO2H absorption near 170 δ in the 13C spectrum.
Problem 21-1
(a) Methylpentanoyl chloride
(b) Cyclohexylacetamide
(c) Isopropyl 2-methylpropanoate
(d) Benzoic anhydride
(e) Isopropyl cyclopentanecarboxylate
(f) Cyclopentyl 2-methylpropanoate
(g) N -Methyl-4-pentenamide
(h) ( R )-2-Hydroxypropanoyl phosphate
(i) Ethyl 2,3-dimethyl-2-butenethioate
Problem 21-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image200-9.jpeg)
Problem 21-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image208-2.jpeg)
Problem 21-4
(a) Acetyl chloride > Methyl acetate > Acetamide
(b) Hexafluoroisopropyl acetate > 2,2,2-Trichloroethyl acetate > Ethyl acetate
Problem 21-5
(a) CH3CO2– Na+
(b) CH3CONH2
(c) CH3CO2CH3 + CH3CO2– Na+
(d) CH3CONHCH3
Problem 21-6
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image209-2.jpeg)
Problem 21-7
(a) Acetic acid + 1-butanol
(b) Butanoic acid + methanol
(c) Cyclopentanecarboxylic acid + isopropyl alcohol
Problem 21-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image210-2.jpeg)
Problem 21-9
(a) Propanoyl chloride + methanol (b) Acetyl chloride + ethanol (c) Benzoyl chloride + ethanol
Problem 21-10
Benzoyl chloride + cyclohexanol
Problem 21-11
This is a typical nucleophilic acyl substitution reaction, with morpholine as the nucleophile and chloride as the leaving group.
Problem 21-12
(a) Propanoyl chloride + methylamine (b) Benzoyl chloride + diethylamine (c) Propanoyl chloride + ammonia
Problem 21-13
(a) Benzoyl chloride + [(CH3)2CH]2CuLi, or 2-methylpropanoyl chloride + Ph2CuLi
Propenoyl chloride + (CH3CH2CH2)2CuLi, or butanoyl chloride + (H2C=CH)2CuLi
Problem 21-14
This is a typical nucleophilic acyl substitution reaction, with p -hydroxyaniline as the nucleophile and acetate ion as the leaving group.
Problem 21-15
Monomethyl ester of benzene-1,2-dicarboxylic acid
Problem 21-16
Reaction of a carboxylic acid with an alkoxide ion gives the carboxylate ion.
Problem 21-17
LiAlH4 gives HOCH2CH2CH2CH2OH; DIBAH gives HOCH2CH2CH2CHO.
Problem 21-18
(a) CH3CH2CH2CH(CH3)CH2OH + CH3OH (b) PhOH + PhCH2OH
Problem 21-19
(a) Ethyl benzoate + 2 CH3MgBr (b) Ethyl acetate + 2 PhMgBr (c) Ethyl pentanoate + 2 CH3CH2MgBr
Problem 21-20
(a) H2O, NaOH
(b) Benzoic acid + LiAlH4
Problem 21-21
1. Mg; 2. CO2, then H3O+; 3. SOCl2; 4. (CH3)2NH; 5. LiAlH4
Problem 21-22
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image211-2.jpeg)
Problem 21-23
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image212-2.jpeg)
Problem 21-24
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image215-2.jpeg)
Problem 21-25
(b) Acid chloride
(c) Carboxylic acid
(d) Aliphatic ketone or cyclohexanone
Problem 21-26
(a) CH3CH2CH2CO2CH2CH3 and other possibilities
(b) CH3CON(CH3)2
(c) CH3CH=CHCOCl or H2C=C(CH3)COCl
Problem 22-1
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image216-2.jpeg)
Problem 22-2
(a) 4 (b) 3 (c) 3 (d) 2 (e) 4 (f) 5
Problem 22-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image222-1.jpeg)
Problem 22-4
Acid-catalyzed formation of an enol is followed by deuteronation of the enol double bond and dedeuteronation of oxygen.
Problem 22-5
1. Br2; 2. Pyridine, heat
Problem 22-6
The intermediate α -bromo acid bromide undergoes a nucleophilic acyl substitution reaction with methanol to give an α -bromo ester.
Problem 22-7
(a) CH3CH2CHO
(b) (CH3)3CCOCH3
(c) CH3CO2H
(d) PhCONH2
(e) CH3CH2CH2CN
(f) CH3CON(CH3)2
Problem 22-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image223-1.jpeg)
Problem 22-9
Acid is regenerated, but base is used stoichiometrically.
Problem 22-10
(a) 1. Na+ −OEt; 2. PhCH2Br; 3. H3O+
(b) 1. Na+ −OEt; 2. CH3CH2CH2Br; 3. Na+ −OEt; 4. CH3Br; 5. H3O+
(c) 1. Na+ −OEt; 2. (CH3)2CHCH2Br; 3. H3O+
Problem 22-11
Malonic ester has only two acidic hydrogens to be replaced.
Problem 22-12
1. Na+ −OEt; 2. (CH3)2CHCH2Br; 3. Na+ −OEt; 4. CH3Br; 5. H3O+
Problem 22-13
(a) (CH3)2CHCH2Br
(b) PhCH2CH2Br
Problem 22-14
None can be prepared.
Problem 22-15
1. 2 Na+ −OEt; 2. BrCH2CH2CH2CH2Br; 3. H3O+
Problem 22-16
(a) Alkylate phenylacetone with CH3I
(b) Alkylate pentanenitrile with CH3CH2I
(c) Alkylate cyclohexanone with H2C═CHCH2Br
(d) Alkylate cyclohexanone with excess CH3I
(e) Alkylate C6H5COCH2CH3 with CH3I
(f) Alkylate methyl 3-methylbutanoate with CH3CH2I
Problem 23-1
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image224-1.jpeg)
Problem 23-2
The reverse reaction is the exact opposite of the forward reaction shown in Figure 23.2.
Problem 23-3 (a)
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image227-1.jpeg)
Problem 23-4
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image230-1.jpeg)
Problem 23-5
(a) Not an aldol product
(b) Pentanone
Problem 23-6
1. NaOH; 2. LiAlH4; 3. H2/Pd
Problem 23-7
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image231-1.jpeg)
Problem 23-8
(a) C6H5CHO + CH3COCH3
(b) Not easily prepared
(c) Not easily prepared
Problem 23-9
The CH2 position between the two carbonyl groups is so acidic that it is completely deprotonated to give a stable enolate ion.
Problem 23-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image232-1.jpeg)
Problem 23-11
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image233-1.jpeg)
Problem 23-12
The cleavage reaction is the exact reverse of the forward reaction.
Problem 23-13
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image236-1.jpeg)
Problem 23-14
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image237-1.jpeg)
Problem 23-15
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image238-1.jpeg)
Problem 23-16
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image239-1.jpeg)
Problem 23-17
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image242-1.jpeg)
Problem 23-18
CH3CH2COCH═CH2 + CH3CH2NO2
Problem 23-19
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image244-1.jpeg)
Problem 23-20
(a) Cyclopentanone enamine + propenenitrile
(b) Cyclohexanone enamine + methyl propenoate
Problem 23-21
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image247-1.jpeg)
Problem 23-22
2,5,5-Trimethyl-1,3-cyclohexanedione + 1-penten-3-one
Problem 24-1
(a) N -Methylethylamine
(b) Tricyclohexylamine
(c) N -Ethyl- N -methylcyclohexylamine
(d) N -Methylpyrrolidine
(e) Diisopropylamine
(f) 1,3-Butanediamine
Problem 24-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image248-1.jpeg)
Problem 24-3 (a)
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image254-1.jpeg)
Problem 24-4
(a) CH3CH2NH2
(c) CH3NHCH3
Problem 24-5
Propylamine is stronger; benzylamine p K b = 4.67; propylamine p K b = 3.29
Problem 24-6
(a) Nitroaniline < p -Aminobenzaldehyde < p -Bromoaniline
(b) p -Aminoacetophenone < p -Chloroaniline < p -Methylaniline
(c) p -(Trifluoromethyl)aniline < p -(Fluoromethyl)aniline < p -Methylaniline
Problem 24-7
Pyrimidine is essentially 100% neutral (unprotonated).
Problem 24-8
(a) Propanenitrile or propanamide
(b) N -Propylpropanamide
(c) Benzonitrile or benzamide
(d) N -Phenylacetamide
Problem 24-9
The reaction takes place by two nucleophilic acyl substitution reactions.
Problem 24-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image258-1.jpeg)
Problem 24-11
(a) Ethylamine + acetone, or isopropylamine + acetaldehyde
(b) Aniline + acetaldehyde
(c) Cyclopentylamine + formaldehyde, or methylamine + cyclopentanone
Problem 24-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image259-1.jpeg)
Problem 24-13
(a) 4,4-Dimethylpentanamide or 4,4-dimethylpentanoyl azide
(b) p -Methylbenzamide or p -methylbenzoyl azide
Problem 24-14
(a) 3-Octene and 4-octene (b) Cyclohexene (c) 3-Heptene (d) Ethylene and cyclohexene
Problem 24-15
H2C═CHCH2CH2CH2N(CH3)2
Problem 24-16
1. HNO3, H2SO4; 2. H2/PtO2; 3. (CH3CO)2O; 4. HOSO2Cl; 5. aminothiazole; 6. H2O, NaOH
Problem 24-17
(a) 1. HNO3, H2SO4; 2. H2/PtO2; 3. 2 CH3Br
(b) 1. HNO3, H2SO4; 2. H2/PtO2; 3. (CH3CO)2O; 4. Cl2; 5. H2O, NaOH
(c) 1. HNO3, H2SO4; 2. Cl2, FeCl3; 3. SnCl2
(d) 1. HNO3, H2SO4; 2. H2/PtO2; 3. (CH3CO)2O; 4. 2 CH3Cl, AlCl3; 5. H2O, NaOH
Problem 24-18
(a) 1. CH3Cl, AlCl3; 2. HNO3, H2SO4; 3. SnCl2; 4. NaNO2, H2SO4; 5. CuBr; 6. KMnO4, H2O
(b) 1. HNO3, H2SO4; 2. Br2, FeBr3; 3. SnCl2, H3O+; 4. NaNO2, H2SO4; 5. CuCN; 6. H3O+
(c) 1. HNO3, H2SO4; 2. Cl2, FeCl3; 3. SnCl2; 4. NaNO2, H2SO4; 5. CuBr
(d) 1. CH3Cl, AlCl3; 2. HNO3, H2SO4; 3. SnCl2; 4. NaNO2, H2SO4; 5. CuCN; 6. H3O+
(e) 1. HNO3, H2SO4; 2. H2/PtO2; 3. (CH3CO)2O; 4. 2 Br2; 5. H2O, NaOH; 6. NaNO2, H2SO4; 7. CuBr
Problem 24-19
1. HNO3, H2SO4; 2. SnCl2; 3a. 2 equiv. CH3I; 3b. NaNO2, H2SO4; 4. product of 3a + product of 3b
Problem 24-20
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image260-1.jpeg)
Problem 24-21
% protonated
Problem 24-22
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image261-1.jpeg)
Problem 24-23
The side-chain nitrogen is more basic than the ring nitrogen.
Problem 24-24
Reaction at C2 is disfavored because the aromaticity of the benzene ring is lost.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image262-1.jpeg)
Problem 24-25
(CH3)3CCOCH3 → (CH3)3CCH(NH2)CH3
Problem 25-1 (a) Aldotetrose (b) Ketopentose (c) Ketohexose (d) Aldopentose
Problem 25-2
(a) S (b) R (c) S
Problem 25-3
A, B, and C are the same.
Problem 25-4
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image263-1.jpeg)
Problem 25-5
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image264-1.jpeg)
Problem 25-6
(a) L-Erythrose; 2 S ,3 S (b) D-Xylose; 2 R ,3 S ,4 R (c) D-Xylulose; 3 S ,4 R
Problem 25-7
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image265-1.jpeg)
Problem 25-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image266-1.jpeg)
Problem 25-9
16 D and 16 L aldoheptoses
Problem 25-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image269-1.jpeg)
Problem 25-11
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image270-1.jpeg)
Problem 25-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image271-1.jpeg)
Problem 25-13
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image272-1.jpeg)
Problem 25-14
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image273-1.jpeg)
Problem 25-15
α -D-Allopyranose
Problem 25-16
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image274-1.jpeg)
Problem 25-17
D-Galactitol has a plane of symmetry and is a meso compound, whereas D-glucitol is chiral.
Problem 25-18
The −CHO end of L-gulose corresponds to the −CH 2 OH end of D-glucose after reduction.
Problem 25-19
D-Allaric acid has a symmetry plane and is a meso compound, but D-glucaric acid is chiral.
Problem 25-20
D-Allose and D-galactose yield meso aldaric acids; the other six D-hexoses yield optically active aldaric acids.
Problem 25-21
D-Allose + D-altrose
Problem 25-22
Problem 25-23
D-Xylose and D-lyxose
Problem 25-24
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image276-1.jpeg)
Problem 25-25
(a) The hemiacetal ring is reduced. (b) The hemiacetal ring is oxidized. (c) All hydroxyl groups are acetylated.
Problem 26-1
Aromatic: Phe, Tyr, Trp, His; sulfur-containing: Cys, Met; alcohols: Ser, Thr; hydrocarbon side chains: Ala, Ile, Leu, Val, Phe
Problem 26-2
The sulfur atom in the −CH2SH group of cysteine makes the side chain higher in ranking than the −CO2H group.
Problem 26-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image277-1.jpeg)
Problem 26-4
Net positive at pH = 5.3; net negative at pH = 7.3
Problem 26-5
(a) Start with 3-phenylpropanoic acid: 1. Br2, PBr3; 2. NH3
(b) Start with 3-methylbutanoic acid: 1. Br2, PBr3; 2. NH3
Problem 26-6
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image278-1.jpeg)
Problem 26-7
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image282-1.jpeg)
Problem 26-8
Val-Tyr-Gly (VYG), Tyr-Gly-Val (YGV), Gly-Val-Tyr (GVY), Val-Gly-Tyr (VGY), Tyr-Val-Gly (YVG), Gly-Tyr-Val (GYV)
Problem 26-9
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image283-1.jpeg)
Problem 26-10
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image284-1.jpeg)
Problem 26-11
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image285-1.jpeg)
Problem 26-12
Trypsin: Asp-Arg + Val-Tyr-Ile-His-Pro-Phe Chymotrypsin: Asp-Arg-Val-Tyr + Ile-His-Pro-Phe
Problem 26-13
Problem 26-14
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image286-1.jpeg)
Problem 26-15
(a) Arg-Pro-Leu-Gly-Ile-Val (b) Val-Met-Trp-Asp-Val-Leu (VMWNVL)
Problem 26-16
This is a typical nucleophilic acyl substitution reaction, with the amine of the amino acid as the nucleophile and tert -butyl carbonate as the leaving group. The tert -butyl carbonate then loses CO2 and gives tert -butoxide, which is protonated.
Problem 26-17
Protect the amino group of leucine.
Protect the carboxylic acid group of alanine.
Couple the protected amino acids with DCC.
Remove the leucine protecting group.
Remove the alanine protecting group.
Problem 26-18
(a) Lyase (b) Hydrolase (c) Oxidoreductase
Problem 27-1
CH3(CH2)18CO2CH2(CH2)30CH3
Problem 27-2
Glyceryl tripalmitate is higher melting.
Problem 27-3
[CH3(CH2)7CH═CH(CH2)7CO2−]2 Mg2+
Problem 27-4
Glyceryl dioleate monopalmitate → glycerol + 2 sodium oleate + sodium palmitate
Problem 27-5
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image287-1.jpeg)
Problem 27-6
The pro- S hydrogen is cis to the −CH3 group; the pro- R hydrogen is trans.
Problem 27-7
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image288-1.jpeg)
Problem 27-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image290-1.jpeg)
Problem 27-9
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image292-1.jpeg)
Problem 27-10
Three methyl groups are removed, the side-chain double bond is reduced, and the double bond in the B ring is migrated.
Problem 28-1
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image293-1.jpeg)
Problem 28-2
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image294-1.jpeg)
Problem 28-3
(5′) ACGGATTAGCC (3′)
Problem 28-4
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image295-1.jpeg)
Problem 28-5
(3′) CUAAUGGCAU (5′)
Problem 28-6
(5′) ACTCTGCGAA (3′)
Problem 28-7
(a) GCU, GCC, GCA, GCG
(b) UUU, UUC
(c) UUA, UUG, CUU, CUC, CUA, CUG
(d) UAU, UAC
Problem 28-8
(a) AGC, GGC, UGC, CGC
(b) AAA, GAA
(c) UAA, CAA, GAA, GAG, UAG, CAG
(d) AUA, GUA
Problem 28-9
Leu-Met-Ala-Trp-Pro-Stop
Problem 28-10
(5′) TTA-GGG-CCA-AGC-CAT-AAG (3′)
Problem 28-11
The cleavage is an SN1 reaction that occurs by protonation of the oxygen atom followed by loss of the stable triarylmethyl carbocation.
Problem 28-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image296-1.jpeg)
Problem 29-1
HOCH2CH(OH)CH2OH + ATP → HOCH2CH(OH)CH2OPO32− + ADP
Problem 29-2
Caprylyl CoA → Hexanoyl CoA → Butyryl CoA → 2 Acetyl CoA
Problem 29-3
(a) 8 acetyl CoA; 7 passages (b) 10 acetyl CoA; 9 passages
Problem 29-4
The dehydration is an E1cB reaction.
Problem 29-5
At C2, C4, C6, C8, and so forth
Problem 29-6
The Si face
Problem 29-7
Steps 7 and 10
Problem 29-8
Steps 1, 3: Phosphate transfers; steps 2, 5, 8: isomerizations; step 4: retro-aldol reaction; step 5: oxidation and nucleophilic acyl substitution; steps 7, 10: phosphate transfers; step 9: E1cB dehydration
Problem 29-9
C1 and C6 of glucose become –CH3 groups; C3 and C4 become CO2.
Problem 29-10
Citrate and isocitrate
Problem 29-11
E1cB elimination of water, followed by conjugate addition
Problem 29-12
pro- R ; anti geometry
Problem 29-13
The reaction occurs by two sequential nucleophilic acyl substitutions, the first by a cysteine residue in the enzyme, with phosphate as leaving group, and the second by hydride donation from NADH, with the cysteine residue as leaving group.
Problem 29-14
Initial imine formation between PMP and α -ketoglutarate is followed by double-bond rearrangement to an isomeric imine and hydrolysis.
Problem 29-15
(CH3)2CHCH2COCO2−
Problem 29-16
Problem 30-1
Ethylene: ψ 1 is the HOMO and ψ 2* is the LUMO in the ground state; ψ 2* is the HOMO and there is no LUMO in the excited state. 1,3-Butadiene: ψ 2 is the HOMO and ψ 3* is the LUMO in the ground state; ψ 3* is the HOMO and ψ 4* is the LUMO in the excited state.
Problem 30-2
Disrotatory: cis -5,6-dimethyl-1,3-cyclohexadiene;
conrotatory: trans -5,6-dimethyl-1,3-cyclohexadiene. Disrotatory closure occurs.
Problem 30-3
The more stable of two allowed products is formed.
Problem 30-4
trans -5,6-Dimethyl-1,3-cyclohexadiene; cis -5,6-dimethyl-1,3-cyclohexadiene
Problem 30-5
cis -3,6-Dimethylcyclohexene; trans -3,6-dimethylcyclohexene
Problem 30-6
A [6 + 4] suprafacial cycloaddition
Problem 30-7
An antarafacial [1,7] sigmatropic rearrangement
Problem 30-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image297-1.jpeg)
Problem 30-9
A series of [1,5] hydrogen shifts occur.
Problem 30-10
o -(1-Methylallyl)phenol
Problem 30-11
Claisen rearrangement is followed by a Cope rearrangement.
Problem 30-12
(a) Conrotatory (b) Disrotatory (c) Suprafacial (d) Antarafacial (e) Suprafacial
Problem 31-1
H2C═CHCO2CH3 < H2C═CHCl < H2C═CHCH3 < H2C═CH–C6H5
Problem 31-2
H2C═CHCH3 < H2C═CHC6H5 < H2C═CHC≡N
Problem 31-3
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image298-1.jpeg)
Problem 31-4
The polymer has no chirality centers.
Problem 31-5
The polymers are racemic and have no optical rotation.
Problem 31-6
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image299-1.jpeg)
Problem 31-7
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image300-1.jpeg)
Problem 31-8
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image301-1.jpeg)
Problem 31-9
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image302.jpeg)
Problem 31-10
Vestenamer: ADMET polymerization of 1,9-decadiene or ROMP of cyclooctene; Norsorex: ROMP of norbornene.
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image303.jpeg)
Problem 31-11
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image304.jpeg)
Problem 31-12
![organic chemistry chapter 10 homework answers image](https://ncstate.pressbooks.pub/app/uploads/sites/52/2023/11/image305.jpeg)
Organic Chemistry: A Tenth Edition - OpenStax adaptation 1 Copyright © by David Tully is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License , except where otherwise noted.
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Organic chemistry
A brief introduction to organic chemistry, unit 1: structure and bonding, unit 2: resonance and acid-base chemistry, unit 3: alkanes, cycloalkanes, and functional groups, unit 4: stereochemistry, unit 5: substitution and elimination reactions, unit 6: alkenes and alkynes, unit 7: alcohols, ethers, epoxides, sulfides, unit 8: conjugated systems and pericyclic reactions, unit 9: aromatic compounds, unit 10: aldehydes and ketones, unit 11: carboxylic acids and derivatives, unit 12: alpha carbon chemistry, unit 13: amines, unit 14: spectroscopy.
What might be a suitable solvent for vegetable oil? Owater saline solution Ovinegar milk gasoline
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A: If you have any questions let me know in comment box thankyou for your question.
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- List the differences and similarities between prescription and over-the-counter (OTC) medicines. Next, list what both types of medicines have in common. Which of the following is true about fluoride treatment of teeth? Fluoride treatment prevents bacterial production of lactic acid. Fluoride treatment prevents bacterial growth on the surface of the tooth. Fluoride treatment prevents lactic acid reacting with the surface of the tooth. Fluoride treatment creates a protective layer on the surface of the tooth known as hydroxylapatite. Fluoride treatment neutralizes lactic acid. Explain the difference between soaps and detergents.
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1.7: Answers to Practice Questions Chapter 1
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![Xin Liu](https://biz.libretexts.org/@api/deki/files/5084/girl-160172__340.png)
- Kwantlen Polytechnic University via Kwantlen Polytechnic University
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Answers to Practice Questions Chapter 1
1.1 Number of valence electrons:
B: 3 valence electrons
N: 5 valence electrons
O: 6 valence electrons
Cl: 7 valence electrons
Mg: 2 valence electrons
- Identify the following bond is “polar” or “non-polar”?
C-C: non-polar C-H : non-polar (very close electronegativity for C and H)
B-F : polar. O-O : non-polar C=N : polar
- Rank the following bonds in the order of increasing bonding polarity: C—S, C—O, C—F (referring to the trend of EN, no need to use the exact EN values).
bonding polarity: C—S < C—O < C—F
![organic chemistry chapter 10 homework answers ""](https://chem.libretexts.org/@api/deki/files/397243/Practice-answer-N2.png?revision=1)
1.4 Why following structure is not the best way to show the Lewis structure of CO 2 ?
![organic chemistry chapter 10 homework answers ""](https://chem.libretexts.org/@api/deki/files/397244/Practice-answer-CO2.png?revision=1)
Because the formal charges are not minimized in above structure. The formal charge in the best Lewis structure of CO 2 are all zero, and the best Lewis structure of CO 2 is shown here:
![organic chemistry chapter 10 homework answers ""](https://chem.libretexts.org/@api/deki/files/397245/Practice-answer-CO2-best.png?revision=1)
1.5 Draw all the equivalent resonance structures for following species. Include any non-zero formal charges in the structures.
- O 3 molecule
![organic chemistry chapter 10 homework answers ""](https://chem.libretexts.org/@api/deki/files/397246/practice-answer-O3.png?revision=1)
- nitrate anion NO 3 –
![organic chemistry chapter 10 homework answers ""](https://chem.libretexts.org/@api/deki/files/397247/practice-answer-NO3.png?revision=1)
- chlorate anion ClO 3 –
![organic chemistry chapter 10 homework answers ""](https://chem.libretexts.org/@api/deki/files/397248/Practice-answer-ClO3-best.png?revision=1)
1.6 Draw all the resonance structures for azide anion, N 3 – , and indicate the most stable one.
![organic chemistry chapter 10 homework answers ""](https://chem.libretexts.org/@api/deki/files/397249/Practice-answer-N3-best.png?revision=1)
1.7 Draw new resonance structure and compare the relative stability, show arrows in the original structure.
![organic chemistry chapter 10 homework answers ""](https://chem.libretexts.org/@api/deki/files/397250/Practice-answer-resonance-1.png?revision=1)
- What is the hybridization of oxygen atom in H 2 O molecule?
![organic chemistry chapter 10 homework answers four electron groups around central oxygen (2 BP, 2LP), the oxygen is in sp3 hybridization](https://chem.libretexts.org/@api/deki/files/397252/Practice-answer-H2O.png?revision=1)
- What is the hybridization of xenon atom in XeF 4 molecule, and what is the shape of the whole molecule?
![organic chemistry chapter 10 homework answers six electron groups around central oxygen (4 BP, 2 LP), the oxygen is in sp3d2 hybridization](https://chem.libretexts.org/@api/deki/files/397253/Practice-answer-XeF4.png?revision=1)
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Why This Chapter? 2.1 Polar Covalent Bonds and Electronegativity; 2.2 Polar Covalent Bonds and Dipole Moments; 2.3 Formal Charges; 2.4 Resonance; 2.5 Rules for Resonance Forms; 2.6 Drawing Resonance Forms; 2.7 Acids and Bases: The Brønsted-Lowry Definition; 2.8 Acid and Base Strength; 2.9 Predicting Acid-Base Reactions from pK a Values; 2.10 Organic Acids and Organic Bases; 2.11 Acids and ...
Now, with expert-verified solutions from Organic Chemistry 10th Edition, you'll learn how to solve your toughest homework problems. Our resource for Organic Chemistry includes answers to chapter exercises, as well as detailed information to walk you through the process step by step. With Expert Solutions for thousands of practice problems ...
1LGP. Step-by-step solution. Step 1 of 5. Halogenation of alkanes takes place via free radical mechanism. Free radical is an intermediate species which is formed during the course of reaction in order to form the haloalkanes. Step 2 of 5. (a) Cis-1,3-dimethyl cyclohexane is a cyclic alkane which on reaction with bromine forms a mixture of ...
Chapter 29: At Quizlet, we're giving you the tools you need to take on any subject without having to carry around solutions manuals or printing out PDFs! Now, with expert-verified solutions from Organic Chemistry 6th Edition, you'll learn how to solve your toughest homework problems. Our resource for Organic Chemistry includes answers to ...
Find step-by-step solutions and answers to Organic Chemistry - 9780321971371, as well as thousands of textbooks so you can move forward with confidence. ... Chapter 10:Structure and Synthesis of Alcohols. Exercise 1a. Exercise 1b. Exercise 1c. Exercise 1d. Exercise 1e. Exercise 1f. Exercise 2a. Exercise 2b. Exercise 2c. Exercise 2d. Exercise 3a ...
Chapter. CH10. Problem. 1P. Step-by-step solution. Step 1 of 3. Alkenes are the class of compounds that consist of a carbon-carbon double bond. Alkenes are further classified in two class: terminal alkenes are those in which double bond is present at the end of the carbon chain whereas non-terminal alkenes are those in which double bond is ...
Answers to Chapter 10 Practice Questions. 10.1 Show the structure of the major product for the following addition reactions. 10.2 For the addition of HBr to 3-methyl-1-butene, two products were observed. Show the reaction mechanism to explain the formation of both products. 10.3 Show major product (s) for the following reactions. 10.4 Show ...
Page ID. Xin Liu. Kwantlen Polytechnic University via Kwantlen Polytechnic University. 10.1 Show structure of the major product for following addition reactions. 10.2 For the addition of HBr to 3-methyl-1-butene, two products were observed. Show the reaction mechanism to explain the formation of both products.
Step-by-step solution. Step 1 of 4. a. The IUPAC name of the compound is 3-hydroxyhexanoic acid. So, the functional group present in this compound is carboxylic acid. The parent name 'hexan' suggests there are six carbon atoms in the main carbon chain of the compound. 3-hydroxy indicates the presence of hydroxyl group at 3 rd carbon atom.
Organic Chemistry, 8e (Wade) Chapter 10 Structure and Synthesis of Alcohols _____, also known as wood alcohol, is used as a fuel and as a solvent. Ingestion of this alcohol can lead to blindness and death. Answer: Methanol or methyl alcohol Diff: 1 Section: 10. _____ is dissolved in water to make the solution sold commercially as rubbing alcohol.
Purdue University. Purdue Chem 26100: Organic Chemistry I (Wenthold) Chapter 10: Alcohols. Chapter 10 Outline. Expand/collapse global location.
Find step-by-step solutions and answers to Organic Chemistry - 9780134042282, as well as thousands of textbooks so you can move forward with confidence. ... Chapter 10:Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds. Exercise 1. Exercise 2. Exercise 3. ... Now, with expert-verified solutions from Organic ...
Chapter 1. C2H7 has too many hydrogens for a compound with two carbons. The CH3 carbon is sp 3; the double-bond carbons are sp 2; the C=C−C and C=C−H bond angles are approximately 120°; other bond angles are near 109°. All carbons are sp 2, and all bond angles are near 120°. All carbons except CH3 are sp 2.
S20.4.10. the carbon in CO 32−, initially at sp2, changes hybridization to sp in CO 2. This page titled 21.E: Organic Chemistry (Exercises) is shared under a CC BY license and was authored, remixed, and/or curated by OpenStax. These are homework exercises to accompany the Textmap created for "Chemistry" by OpenStax.
Step-by-step solution. Step 1 of 1. Carbon is belongs to 4A group. Its atomic number is 6. So, the carbon has 6 electrons. Its electronic configuration is . In the carbon atom, the outer most orbitals (valence orbitals) are . These are second-row orbitals. Therefore, the valence electrons present in outer most orbitals () are 4.
A brief introduction to organic chemistry. Carbon can form covalent bonds with itself and other elements to create a mind-boggling array of structures. In organic chemistry, we will learn about the reactions chemists use to synthesize crazy carbon based structures, as well as the analytical methods to characterize them.
Textbook solutions for Organic Chemistry 8th Edition William H. Brown and others in this series. View step-by-step homework solutions for your homework. Ask our subject experts for help answering any of your homework questions!
Find step-by-step solutions and answers to Organic Chemistry - 9781118452288, as well as thousands of textbooks so you can move forward with confidence. ... Chapter 10:Alkynes. Exercise 1a. Exercise 1b. Exercise 1c. Exercise 1d. Exercise 1e. Exercise 1f. Exercise 1g. Exercise 2a. Exercise 2b. Exercise 3. Exercise 4. Exercise 5a. Exercise 5b ...
Q: 43 2.33 points use q = mc Dt for this problem: 10 g of Ethanol (specific heat = 2.42 J/g degreeC) is… A: The problem is asking for the change in temperature when 10 g of Ethanol is heated and releases 242J…
Step-by-step solution. Step 1 of 9. a. The first step to determine the constitution of the following compounds is by determining the amount of bonds each compound can form. In CH 4 O, carbon can form four bonds, hydrogen can form one bond, and oxygen can form two bonds. Step 2 of 9. Atoms that can form the most bonds should be placed in the ...
1.7 Draw new resonance structure and compare the relative stability, show arrows in the original structure. 1.8. What is the hybridization of oxygen atom in H 2 O molecule? What is the hybridization of xenon atom in XeF 4 molecule, and what is the shape of the whole molecule?
Benzylic Group. An atom or group bonded to an spy hybridized carbon adjacent to a benzene ring. Benzylic Radicals. Due to the adjacent benzene ring, have greater possibility for delocalization than allylic radicals. Study with Quizlet and memorize flashcards containing terms like Production of Radicals, Peroxides, Halogens and more.
(8-10:00am) NOTE: The material covered on each exam may be revised if necessary. Homework: Although homework is not a part of the grade, students are strongly advised to work problems within the text of each chapter and at the end of each chapter. Work them with the Solutions Manual CLOSED. Quizzes: Quizzes are posted on the class webpage ...
At Quizlet, we're giving you the tools you need to take on any subject without having to carry around solutions manuals or printing out PDFs! Now, with expert-verified solutions from Organic Chemistry 12th Edition, you'll learn how to solve your toughest homework problems. Our resource for Organic Chemistry includes answers to chapter ...