Chapter 16 -

PROBLEM $o$-xylene: $2 ; p$-xylene: $1 ; m$-xylene: 3
16-3
PROBLEM $\mathrm{D}^{+}$does electrophilic substitutions on the ring.
16-4
PROBLEM No rearrangement: (a), (b), (e)
16-5
PROBLEM tert-Butylbenzene
16-6
PROBLEM (a) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCOCl}$ (b) PhCOCl
16-7
PROBLEM (a) Phenol $>$ Toluene $>$ Benzene $>$ Nitrobenzene
16-8 (b) Phenol $>$ Benzene $>$ Chlorobenzene $>$ Benzoic acid
(c) Aniline $>$ Benzene $>$ Bromobenzene $>$ Benzaldehyde

PROBLEM (a) $o$ - and $p$-Bromonitrobenzene (b) $m$-Bromonitrobenzene (c) $o$ - and $p$-Chlorophenol
16-9 (d) $o$ - and $p$-Bromoaniline
PROBLEM Alkylbenzenes are more reactive than benzene itself, but acylbenzenes are less reactive. 16-10

PROBLEM Toluene is more reactive; the trifluoromethyl group is electron-withdrawing. 16-11
PROBLEM The nitrogen electrons are donated to the nearby carbonyl group by resonance and are less 16-12 available to the ring.
PROBLEM The meta intermediate is most favored. 16-13
PROBLEM
(a) Ortho and para to $-\mathrm{OCH}_{3}$
(b) Ortho and para to $-\mathrm{NH}_{2}$
(c) Ortho and para to -Cl 16-14
PROBLEM (a) Reaction occurs ortho and para to the $-\mathrm{CH}_{3}$ group.
16-15 (b) Reaction occurs ortho and para to the $-\mathrm{OCH}_{3}$ group.
PROBLEM The phenol is deprotonated by KOH to give an anion that carries out a nucleophilic acyl substitution 16-16 reaction on the fluoronitrobenzene.
PROBLEM Only one benzyne intermediate can form from $p$-bromotoluene; two different benzyne 16-17 intermediates can form from $m$-bromotoluene.
PROBLEM (a) m-Nitrobenzoic acid (b) p-tert-Butylbenzoic acid 16-18
PROBLEM A benzyl radical is more stable than a primary alkyl radical by $52 \mathrm{~kJ} / \mathrm{mol}$ and is similar in stability 16-19 to an allyl radical.
PROBLEM 1. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}, \mathrm{AlCl}_{3} ; 2$. NBS; 3. KOH , ethanol 16-20
PROBLEM 1. $\mathrm{PhCOCl}, \mathrm{AlCl}_{3} ; 2 . \mathrm{H}_{2} / \mathrm{Pd}$ 16-21
PROBLEM (a) 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{Cl}_{2}, \mathrm{FeCl}_{3}$ (b) 1. $\mathrm{CH}_{3} \mathrm{COCl}, \mathrm{AlCl}_{3} ; 2 . \mathrm{Cl}_{2}, \mathrm{FeCl}_{3} ; 3 . \mathrm{H} 2 / \mathrm{Pd}$
16-22 (c) 1. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCl}, \mathrm{AlCl}_{3} ; 2 . \mathrm{Cl}_{2}, \mathrm{FeCl}_{3} ; 3 . \mathrm{H}_{2} / \mathrm{Pd} ; 4 . \mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4}$
(d) 1. $\mathrm{CH}_{3} \mathrm{Cl}, \mathrm{AlCl}_{3} ; 2 . \mathrm{Br}_{2}, \mathrm{FeBr}_{3} ; 3 . \mathrm{SO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4}$


Chapter 16 -

PROBLEM (a) Friedel-Crafts acylation does not occur on a deactivated ring.
16-23 (b) Rearrangement occurs during Friedel-Crafts alkylation with primary halides; chlorination occurs ortho to the alkyl group.


Chapter 16 -


Chapter 16 -

PROBLEM Hydrogen-bonding is more difficult in hindered alcohols.
17-3
PROBLEM (a) $\mathrm{HC} \equiv \mathrm{CH}<\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH}<\mathrm{CH}_{3} \mathrm{OH}<\left(\mathrm{CF}_{3}\right)_{2} \mathrm{CHOH}$
17-4 (b) $p$-Methylphenol < Phenol < p-(Trifluoromethyl)phenol
(c) Benzyl alcohol < Phenol < p-Hydroxybenzoic acid


Chapter 16 -

PROBLEM The electron-withdrawing nitro group stabilizes an alkoxide ion, but the electron-donating
17-5 methoxyl group destabilizes the anion.
PROBLEM (a) 2-Methyl-3-pentanol (b) 2-Methyl-4-phenyl-2-butanol (c) meso-5,6-Decanediol 17-6
PROBLEM (a) $\mathrm{NaBH}_{4}$ (b) $\mathrm{LiAlH}_{4}$ (c) $\mathrm{LiAlH}_{4}$


Chapter 16 -

17-7
PROBLEM (a) Benzaldehyde or benzoic acid (or ester) (b) Acetophenone (c) Cyclohexanone
17-8 (d) 2-Methylpropanal or 2-methylpropanoic acid (or ester)
PROBLEM (a) 1-Methylcyclopentanol (b) 1,1-Diphenylethanol (c) 3-Methyl-3-hexanol
17-9
PROBLEM (a)
17-10
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1186.jpg?height=134&width=385&top_left_y=426&top_left_x=477)
or
<img class="imgSvg" id = "m6sn3qrhkuxy593mtl" src="data:image/svg+xml;base64,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Chapter 16 -

PROBLEM Cyclohexanone $+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}$ 17-11
PROBLEM 1. $p$-TosCl, pyridine; 2. NaCN 17-12
PROBLEM (a) 2-Methyl-2-pentene (b) 3-Methylcyclohexene (c) 1-Methylcyclohexene 17-13 (d) 2,3-Dimethyl-2-pentene (e) 2-Methyl-2-pentene
PROBLEM (a) 1-Phenylethanol (b) 2-Methyl-1-propanol (c) Cyclopentanol 17-14
PROBLEM (a) Hexanoic acid, hexanal (b) 2-Hexanone (c) Hexanoic acid, no reaction 17-15
PROBLEM $\mathrm{S}_{\mathrm{N}} 2$ reaction of $\mathrm{F}^{-}$on silicon with displacement of alkoxide ion. 17-16
PROBLEM Protonation of 2-methylpropene gives the tert-butyl cation, which carries out an electrophilic 17-17 aromatic substitution reaction.
PROBLEM Disappearance of -OH absorption; appearance of $\mathrm{C}=\mathrm{O}$ 17-18
PROBLEM (a) Singlet (b) Doublet (c) Triplet (d) Doublet (e) Doublet (f) Singlet 17-19


Chapter 18 -

PROBLEM (a) Diisopropyl ether (b) Cyclopentyl propyl ether
18-1 (c) $p$-Bromoanisole or 4-bromo-1-methoxybenzene
(d) 1-Methoxycyclohexene
(e) Ethyl isobutyl ether (f) Allyl vinyl ether


Chapter 18 -

PROBLEM A mixture of diethyl ether, dipropyl ether, and ethyl propyl ether is formed in a $1: 1: 2$ ratio. 18-2
PROBLEM (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{O}^{-}+\mathrm{CH}_{3} \mathrm{Br}$ (b) $\mathrm{PhO}^{-}+\mathrm{CH}_{3} \mathrm{Br}$ (c) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHO}^{-}+\mathrm{PhCH}_{2} \mathrm{Br}$
18-3 (d) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{O}^{-}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Br}$
PROBLEM
18-4
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1187.jpg?height=224&width=806&top_left_y=1788&top_left_x=405)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1187.jpg?height=180&width=733&top_left_y=2038&top_left_x=411)


Chapter 18 -

PROBLEM (a) Either method (b) Williamson (c) Alkoxymercuration (d) Williamson 18-5
PROBLEM (a) Bromoethane $>$ 2-Bromopropane $>$ Bromobenzene
18-6 (b) Bromoethane $>$ Chloroethane $>$ 1-Iodopropene


Chapter 18 -

PROBLEM (a)
18-7
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1188.jpg?height=191&width=429&top_left_y=203&top_left_x=477)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1188.jpg?height=128&width=494&top_left_y=207&top_left_x=973)


Chapter 18 -

PROBLEM Protonation of the oxygen atom, followed by E1 reaction
18-8
PROBLEM $\mathrm{Br}^{-}$and $\mathrm{I}^{-}$are better nucleophiles than $\mathrm{Cl}^{-}$.
18-9
PROBLEM
18-10
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1188.jpg?height=188&width=744&top_left_y=589&top_left_x=398)


Chapter 18 -


Chapter 18 -

PROBLEM (a) 2-Butanethiol (b) 2,2,6-Trimethyl-4-heptanethiol (c) 2-Cyclopentene-1-thiol
18-16 (d) Ethyl isopropyl sulfide (e) o-Di(methylthio)benzene (f) 3-(Ethylthio)cyclohexanone
PROBLEM (a) 1. $\mathrm{LiAlH}_{4} ; 2 . \mathrm{PBr}_{3} ; 3 .\left(\mathrm{H}_{2} \mathrm{~N}\right)_{2} \mathrm{C}=\mathrm{S} ; 4 . \mathrm{H}_{2} \mathrm{O}, \mathrm{NaOH}$
18-17 (b) 1. HBr ; 2. $\left(\mathrm{H}_{2} \mathrm{~N}\right)_{2} \mathrm{C}=\mathrm{S} ; 3 . \mathrm{H}_{2} \mathrm{O}, \mathrm{NaOH}$
PROBLEM 1,2-Epoxybutane
18-18
PROBLEM Acetyl chloride is more electrophilic than acetone.
18-69
PROBLEM
18-70
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1188.jpg?height=177&width=933&top_left_y=2009&top_left_x=406)


Chapter 18 -

PROBLEM (a) Nucleophilic acyl substitution (b) Nucleophilic addition (c) Carbonyl condensation 18-71


Chapter 19 -

PROBLEM (a) 2-Methyl-3-pentanone (b) 3-Phenylpropanal (c) 2,6-Octanedione
19-1 (d) trans-2-Methylcyclohexanecarbaldehyde (e) 4-Hexenal
(f) cis-2,5-Dimethylcyclohexanone


Chapter 19 -


Chapter 19 -

PROBLEM The steps are the exact reverse of the forward reaction shown in Figure 19.7.
19-11
PROBLEM
19-12
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1189.jpg?height=112&width=866&top_left_y=1473&top_left_x=418)


Chapter 19 -

PROBLEM (a) $\mathrm{H}_{2} / \mathrm{Pd}$ (b) $\mathrm{N}_{2} \mathrm{H}_{4}, \mathrm{KOH}$ (c) 1. $\mathrm{H}_{2} / \mathrm{Pd} ; 2 . \mathrm{N}_{2} \mathrm{H}_{4}, \mathrm{KOH}$
19-13
PROBLEM The mechanism is identical to that between a ketone and 2 equivalents of a monoalcohol, shown in
19-14 Figure 19.11.
PROBLEM
19-15
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1189.jpg?height=191&width=587&top_left_y=1783&top_left_x=414)


Chapter 19 -

PROBLEM
(a) Cyclohexanone $+(\mathrm{Ph})_{3} \mathrm{P}=\mathrm{CHCH}_{3}$
(b) Cyclohexanecarbaldehyde $+(\mathrm{Ph})_{3} \mathrm{P}=\mathrm{CH}_{2}$

19-16
(e) Acetone $+(\mathrm{Ph})_{3} \mathrm{P}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$ (d) Acetone $+(\mathrm{Ph})_{3} \mathrm{P}=\mathrm{CHPh}$
(f) 2-Cyclohexenone $+(\mathrm{Ph})_{3} \mathrm{P}=\mathrm{CH}_{2}$


Chapter 19 -

PROBLEM (a) 3-Buten-2-one $+\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2}\right)_{2} \mathrm{CuLi}$ (b) 3-Methyl-2-cyclohexenone $+\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CuLi}$
19-22 (c) 4-tert-Butyl-2-cyclohexenone $+\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{2} \mathrm{CuLi}$ (d) Unsaturated ketone $+\left(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}\right)_{2} \mathrm{CuLi}$
PROBLEM Look for appearance of either an alcohol or a saturated ketone in the product. 19-23
PROBLEM (a) $1715 \mathrm{~cm}^{-1}$ (b) $1685 \mathrm{~cm}^{-1}$ (c) $1750 \mathrm{~cm}^{-1}$ (d) $1705 \mathrm{~cm}^{-1}$ (e) $1715 \mathrm{~cm}^{-1}$ $\mathbf{1 9 - 2 4}$ (f) $1705 \mathrm{~cm}^{-1}$
PROBLEM (a) Different peaks due to McLafferty rearrangement
19-25 (b) Different peaks due to $\alpha$ cleavage and McLafferty rearrangement
(c) Different peaks due to McLafferty rearrangement


Chapter 19 -

PROBLEM IR: $1750 \mathrm{~cm}^{-1}$; MS: 140, 84
19-26


Chapter 20 -

PROBLEM (a) 3-Methylbutanoic acid (b) 4-Bromopentanoic acid (c) 2-Ethylpentanoic acid
20-1 (d) cis-4-Hexenoic acid (e) 2,4-Dimethylpentanenitrile
(f) cis-1,3-Cyclopentanedicarboxylic acid


Chapter 20 -


Chapter 20 -

PROBLEM Dissolve the mixture in ether, extract with aqueous NaOH , separate and acidify the aqueous layer,
20-3 and extract with ether.
PROBLEM 43\%
20-4
PROBLEM (a) $82 \%$ dissociation (b) $73 \%$ dissociation 20-5
PROBLEM Lactic acid is stronger because of the inductive effect of the -OH group.
20-6
PROBLEM The dianion is destabilized by repulsion between charges.
20-7
PROBLEM More reactive
20-8
PROBLEM (a) p-Methylbenzoic acid < Benzoic acid < $p$-Chlorobenzoic acid
20-9 (b) Acetic acid < Benzoic acid < $p$-Nitrobenzoic acid
PROBLEM (a) 1. $\mathrm{Mg} ; 2 . \mathrm{CO}_{2} ; 3 . \mathrm{H}_{3} \mathrm{O}^{+}$(b) 1. $\mathrm{Mg} ; 2 . \mathrm{CO}_{2} ; 3 . \mathrm{H}_{3} \mathrm{O}^{+}$or 1. $\mathrm{NaCN} ; 2 . \mathrm{H}_{3} \mathrm{O}^{+}$ 20-10
PROBLEM 1. NaCN; 2. $\mathrm{H}_{3} \mathrm{O}^{+}$; 3. $\mathrm{LiAlH}_{4}$ 20-11
PROBLEM 1. $\mathrm{PBr}_{3} ; 2 . \mathrm{NaCN} ; 3 . \mathrm{H}_{3} \mathrm{O}^{+} ; 4 . \mathrm{LiAlH}_{4}$
20-12
PROBLEM (a) Propanenitrile $+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}$, then $\mathrm{H}_{3} \mathrm{O}^{+}$(b) $p$-Chlorobenzonitrile $+\mathrm{CH}_{3} \mathrm{MgBr}$, then $\mathrm{H}_{3} \mathrm{O}^{+}$ 20-13
PROBLEM 1. NaCN ; 2. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}$, then $\mathrm{H}_{3} \mathrm{O}^{+}$ 20-14


Chapter 20 -

PROBLEM A carboxylic acid has a very broad -OH absorption at $2500-3300 \mathrm{~cm}^{-1}$.
20-15
PROBLEM 4-Hydroxycyclohexanone: $\mathrm{H}-\mathrm{C}-\mathrm{O}$ absorption near $4 \delta$ in the ${ }^{1} \mathrm{H}$ spectrum and $\mathrm{C}=\mathrm{O}$ absorption near 20-16 $210 \delta$ in the ${ }^{13} \mathrm{C}$ spectrum. Cyclopentanecarboxylic acid: $-\mathrm{CO}_{2} \mathrm{H}$ absorption near $12 \delta$ in the ${ }^{1} \mathrm{H}$ spectrum and $-\mathrm{CO}_{2} \mathrm{H}$ absorption near $170 \delta$ in the ${ }^{13} \mathrm{C}$ spectrum.


Chapter 20 -

Chapter 21
PROBLEM (a) 4-Methylpentanoyl chloride (b) Cyclohexylacetamide (c) Isopropyl 2-methylpropanoate
21-1 (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


Chapter 20 -

PROBLEM
(a) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CO}_{2} \mathrm{C}_{6} \mathrm{H}_{5}$
(b)
$\mathrm{H}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CON}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}_{3}$
(c) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{COCl}$


Chapter 20 -

PROBLEM
21-3
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1191.jpg?height=229&width=1075&top_left_y=1235&top_left_x=414)


Chapter 20 -

PROBLEM (a) Acetyl chloride $>$ Methyl acetate $>$ Acetamide
21-4 (b) Hexafluoroisopropyl acetate $>2,2,2$-Trichloroethyl acetate $>$ Ethyl acetate
PROBLEM
(a) $\mathrm{CH}_{3} \mathrm{CO}_{2}^{-} \mathrm{Na}^{+}$
(b) $\mathrm{CH}_{3} \mathrm{CONH}_{2}$
(c) $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{3}+\mathrm{CH}_{3} \mathrm{CO}_{2}^{-} \mathrm{Na}^{+}$
(d) $\mathrm{CH}_{3} \mathrm{CONHCH}_{3}$


Chapter 20 -

21-5
PROBLEM
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1191.jpg?height=109&width=1018&top_left_y=1680&top_left_x=326)


Chapter 20 -

PROBLEM (a) Propanoyl chloride + methanol (b) Acetyl chloride + ethanol
21-9 (c) Benzoyl chloride + ethanol
PROBLEM Benzoyl chloride + cyclohexanol
21-10
PROBLEM This is a typical nucleophilic acyl substitution reaction, with morpholine as the nucleophile and
21-11 chloride as the leaving group.
PROBLEM (a) Propanoyl chloride + methylamine (b) Benzoyl chloride + diethylamine
21-12 (c) Propanoyl chloride + ammonia
PROBLEM (a) Benzoyl chloride $+\left[\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}\right]_{2} \mathrm{CuLi}$, or 2-methylpropanoyl chloride $+\mathrm{Ph}_{2} \mathrm{CuLi}$
21-13 (b) 2-Propenoyl chloride $+\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2}\right)_{2} \mathrm{CuLi}$, or butanoyl chloride $+\left(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}\right)_{2} \mathrm{CuLi}$
PROBLEM This is a typical nucleophilic acyl substitution reaction, with $p$-hydroxyaniline as the nucleophile


Chapter 20 -

21-14 and acetate ion as the leaving group.
PROBLEM Monomethyl ester of benzene-1,2-dicarboxylic acid
21-15
PROBLEM Reaction of a carboxylic acid with an alkoxide ion gives the carboxylate ion.
21-16
PROBLEM LiAlH 4 gives $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$; DIBAH gives $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHO}$.
21-17
PROBLEM (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{OH}+\mathrm{CH}_{3} \mathrm{OH}$ (b) $\mathrm{PhOH}+\mathrm{PhCH}_{2} \mathrm{OH}$
21-18
PROBLEM (a) Ethyl benzoate $+2 \mathrm{CH}_{3} \mathrm{MgBr}$ (b) Ethyl acetate +2 PhMgBr
21-19 (c) Ethyl pentanoate $+2 \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}$
PROBLEM (a) $\mathrm{H}_{2} \mathrm{O}, \mathrm{NaOH}$ (b) Benzoic acid $+\mathrm{LiAlH}_{4}$ (c) $\mathrm{LiAlH}_{4}$
21-20
PROBLEM 1. Mg; 2. $\mathrm{CO}_{2}$, then $\mathrm{H}_{3} \mathrm{O}^{+}$; 3. $\mathrm{SOCl}_{2}$; 4. $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}$; 5. $\mathrm{LiAlH}_{4}$
21-21
PROBLEM
21-22
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1192.jpg?height=278&width=451&top_left_y=853&top_left_x=409)
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$\downarrow$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1192.jpg?height=209&width=620&top_left_y=1619&top_left_x=411)


Chapter 20 -

PROBLEM (a)
21-23
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1192.jpg?height=104&width=457&top_left_y=1824&top_left_x=479)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1192.jpg?height=150&width=364&top_left_y=1833&top_left_x=1008)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1192.jpg?height=145&width=377&top_left_y=1833&top_left_x=1446)


Chapter 20 -

PROBLEM (a) Ester (b) Acid chloride (c) Carboxylic acid (d) Aliphatic ketone or cyclohexanone
21-25
PROBLEM (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$ and other possibilities (b) $\mathrm{CH}_{3} \mathrm{CON}\left(\mathrm{CH}_{3}\right)_{2}$
21-26 (c) $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCOCl}$ or $\mathrm{H}_{2} \mathrm{C}=\mathrm{C}\left(\mathrm{CH}_{3}\right) \mathrm{COCl}$


Chapter 20 -

PROBLEM
(a) 4
(b) 3
(c) 3
(d) 2
(e) $4 \quad$ (f) 5


Chapter 20 -

22-2
PROBLEM
22-3
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1193.jpg?height=315&width=1308&top_left_y=626&top_left_x=406)


Chapter 20 -

PROBLEM Acid-catalyzed formation of an enol is followed by deuteronation of the enol double bond and
22-4 dedeuteronation of oxygen.
PROBLEM 1. $\mathrm{Br}_{2}$; 2. Pyridine, heat
22-5
PROBLEM The intermediate $\alpha$-bromo acid bromide undergoes a nucleophilic acyl substitution reaction with
22-6 methanol to give an $\alpha$-bromo ester.
PROBLEM (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHO}$ (b) $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCOCH}_{3}$
(c) $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$ (d) $\mathrm{PhCONH}_{2}$ (e) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CN}$

22-7 (f) $\mathrm{CH}_{3} \mathrm{CON}\left(\mathrm{CH}_{3}\right)_{2}$
PROBLEM
22-8 ${ }^{-}: \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{N}: \longleftrightarrow \mathrm{H}_{2} \mathrm{C}=\mathrm{C}=\ddot{\mathrm{N}}:^{-}$
PROBLEM Acid is regenerated, but base is used stoichiometrically.
22-9
PROBLEM (a) 1. $\mathrm{Na}^{+-} \mathrm{OEt}$; 2. $\mathrm{PhCH}_{2} \mathrm{Br}$; 3. $\mathrm{H}_{3} \mathrm{O}^{+}$
22-10 (b) 1. $\mathrm{Na}^{+-}{ }^{-} \mathrm{OEt}$; 2. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$; 3. $\mathrm{Na}^{+{ }^{-}} \mathrm{OEt}$; 4. $\mathrm{CH}_{3} \mathrm{Br} ;$ 5. $\mathrm{H}_{3} \mathrm{O}^{+}$
(c) 1. $\mathrm{Na}^{+-} \mathrm{OEt}$; 2. $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{Br} ; 3 . \mathrm{H}_{3} \mathrm{O}^{+}$

PROBLEM Malonic ester has only two acidic hydrogens to be replaced. 22-11
PROBLEM 1. $\mathrm{Na}^{+-}$OEt; 2. $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{Br}$; 3. $\mathrm{Na}^{+-}{ }^{-} \mathrm{OEt}$; 4. $\mathrm{CH}_{3} \mathrm{Br} ; 5 . \mathrm{H}_{3} \mathrm{O}^{+}$ 22-12
PROBLEM (a) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{Br}$ (b) $\mathrm{PhCH}_{2} \mathrm{CH}_{2} \mathrm{Br}$ 22-13
PROBLEM None can be prepared.
22-14
PROBLEM 1.2 $\mathrm{Na}^{+-} \mathrm{OEt}$; 2. $\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$; 3. $\mathrm{H}_{3} \mathrm{O}^{+}$
22-15
PROBLEM (a) Alkylate phenylacetone with $\mathrm{CH}_{3} \mathrm{I}$ (b) Alkylate pentanenitrile with $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{I}$
22-16 (c) Alkylate cyclohexanone with $\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}_{2} \mathrm{Br}$ (d) Alkylate cyclohexanone with excess $\mathrm{CH}_{3} \mathrm{I}$
(e) Alkylate $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCH}_{2} \mathrm{CH}_{3}$ with $\mathrm{CH}_{3} \mathrm{I}$ (f) Alkylate methyl 3-methylbutanoate with $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{I}$


Chapter 20 -

Chapter 23


Chapter 20 -

PROBLEM The reverse reaction is the exact opposite of the forward reaction shown in Figure 23.2.


Chapter 20 -


Chapter 20 -

PROBLEM
23-4
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1194.jpg?height=234&width=893&top_left_y=463&top_left_x=410)


Chapter 20 -

PROBLEM (a) Not an aldol product (b) 3-Pentanone
23-5
PROBLEM 1. NaOH; 2. $\mathrm{LiAlH}_{4} ; 3 . \mathrm{H}_{2} / \mathrm{Pd}$
23-6
PROBLEM
23-7
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1194.jpg?height=174&width=705&top_left_y=886&top_left_x=401)


Chapter 20 -

PROBLEM
(a) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}+\mathrm{CH}_{3} \mathrm{COCH}_{3}$
(b) Not easily prepared
(c) Not easily prepared


Chapter 20 -

PROBLEM
23-15
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1194.jpg?height=232&width=641&top_left_y=2123&top_left_x=414)


Chapter 20 -

PROBLEM 2,5,5-Trimethyl-1,3-cyclohexanedione + 1-penten-3-one
23-22


Chapter 24 -

PROBLEM (a) $N$-Methylethylamine (b) Tricyclohexylamine (c) $N$-Ethyl- $N$-methylcyclohexylamine
24-1 (d) $N$-Methylpyrrolidine
(e) Diisopropylamine (f) 1,3-Butanediamine


Chapter 24 -


Chapter 24 -

PROBLEM (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}$
(b) NaOH
(c) $\mathrm{CH}_{3} \mathrm{NHCH}_{3}$


Chapter 24 -

24-4
PROBLEM Propylamine is stronger; benzylamine $\mathrm{p} K_{\mathrm{b}}=4.67$; propylamine $\mathrm{p} K_{\mathrm{b}}=3.29$
24-5
PROBLEM (a) $p$-Nitroaniline $<p$-Aminobenzaldehyde $<p$-Bromoaniline
24-6 (b) $p$-Aminoacetophenone $<p$-Chloroaniline $<p$-Methylaniline
(c) $p$-(Trifluoromethyl)aniline $<p$-(Fluoromethyl)aniline $<p$-Methylaniline


Chapter 24 -

PROBLEM Pyrimidine is essentially 100\% neutral (unprotonated).
24-7
PROBLEM (a) Propanenitrile or propanamide (b) $N$-Propylpropanamide (c) Benzonitrile or benzamide
24-8 (d) $N$-Phenylacetamide
PROBLEM The reaction takes place by two nucleophilic acyl substitution reactions.
24-9
PROBLEM
24-10
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1195.jpg?height=164&width=1085&top_left_y=2363&top_left_x=406)


Chapter 24 -

PROBLEM (a) Ethylamine + acetone, or isopropylamine + acetaldehyde (b) Aniline + acetaldehyde
24-11 (c) Cyclopentylamine + formaldehyde, or methylamine + cyclopentanone
PROBLEM
24-12
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1196.jpg?height=145&width=668&top_left_y=296&top_left_x=422)


Chapter 24 -

PROBLEM (a) 4,4-Dimethylpentanamide or 4,4-dimethylpentanoyl azide
24-13 (b) $p$-Methylbenzamide or $p$-methylbenzoyl azide
PROBLEM (a) 3-Octene and 4-octene (b) Cyclohexene (c) 3-Heptene (d) Ethylene and cyclohexene 24-14
PROBLEM $\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{~N}\left(\mathrm{CH}_{3}\right)_{2}$


24-15 -

PROBLEM 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{H}_{2} / \mathrm{PtO}_{2}$; 3. $\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O} ; 4 . \mathrm{HOSO}_{2} \mathrm{Cl}$; 5. aminothiazole; 6. $\mathrm{H}_{2} \mathrm{O}, \mathrm{NaOH}$ 24-16
PROBLEM (a) 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{H}_{2} / \mathrm{PtO}_{2} ; 3.2 \mathrm{CH}_{3} \mathrm{Br}$
24-17 (b) 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{H}_{2} / \mathrm{PtO}_{2}$; 3. $\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O} ; 4 . \mathrm{Cl}_{2} ; 5 . \mathrm{H} 2 \mathrm{O}, \mathrm{NaOH}$
(c) 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{Cl}_{2}, \mathrm{FeCl}_{3} ; 3 . \mathrm{SnCl}_{2}$
(d) 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{H}_{2} / \mathrm{PtO}_{2}$; 3. $\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O} ; 4.2 \mathrm{CH}_{3} \mathrm{Cl}, \mathrm{AlCl}_{3} ; 5 . \mathrm{H}_{2} \mathrm{O}, \mathrm{NaOH}$

PROBLEM (a) 1. $\mathrm{CH}_{3} \mathrm{Cl}, \mathrm{AlCl}_{3} ; 2 . \mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 3 . \mathrm{SnCl}_{2} ; 4 . \mathrm{NaNO}_{2}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 5 . \mathrm{CuBr} ; 6 . \mathrm{KMnO}_{4}, \mathrm{H}_{2} \mathrm{O}$
24-18 (b) 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{Br}_{2}, \mathrm{FeBr}_{3} ; 3 . \mathrm{SnCl}_{2}, \mathrm{H}_{3} \mathrm{O}^{+} ; 4 . \mathrm{NaNO}_{2}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 5 . \mathrm{CuCN} ; 6 . \mathrm{H}_{3} \mathrm{O}^{+}$
(c) 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{Cl}_{2}, \mathrm{FeCl}_{3} ; 3 . \mathrm{SnCl}_{2} ; 4 . \mathrm{NaNO}_{2}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 5 . \mathrm{CuBr}$
(d) 1. $\mathrm{CH}_{3} \mathrm{Cl}, \mathrm{AlCl}_{3} ; 2 . \mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 3 . \mathrm{SnCl}_{2} ; 4 . \mathrm{NaNO}_{2}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 5 . \mathrm{CuCN} ; 6 . \mathrm{H}_{3} \mathrm{O}^{+}$
(e) 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{H}_{2} / \mathrm{PtO}_{2}$; 3. $\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}$; $4.2 \mathrm{Br}_{2}$; 5. $\mathrm{H}_{2} \mathrm{O}, \mathrm{NaOH} ; 6 . \mathrm{NaNO}_{2}, \mathrm{H}_{2} \mathrm{SO}_{4}$; 7. CuBr

PROBLEM 1. $\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 2 . \mathrm{SnCl}_{2}$; 3a. 2 equiv. $\mathrm{CH}_{3} \mathrm{I} ; 3 \mathrm{~b} . \mathrm{NaNO}_{2}, \mathrm{H}_{2} \mathrm{SO}_{4} ; 4$. product of $3 \mathrm{a}+$ product of 3 b 24-19
PROBLEM
24-20
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1196.jpg?height=245&width=426&top_left_y=1284&top_left_x=405)


24-15 -

PROBLEM 4.1\% protonated
24-21
PROBLEM Attack at C2:
24-22
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1196.jpg?height=215&width=1039&top_left_y=1654&top_left_x=402)


24-15 -


24-15 -

PROBLEM The side-chain nitrogen is more basic than the ring nitrogen.


24-15 -

24-23
PROBLEM Reaction at C 2 is disfavored because the aromaticity of the benzene ring is lost. 24-24
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1197.jpg?height=242&width=738&top_left_y=280&top_left_x=401)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1197.jpg?height=223&width=673&top_left_y=284&top_left_x=1146)


24-15 -

PROBLEM $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCOCH}_{3} \rightarrow\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}\left(\mathrm{NH}_{2}\right) \mathrm{CH}_{3}$ 24-25


24-15 -

Chapter 25
PROBLEM (a) Aldotetrose (b) Ketopentose (c) Ketohexose (d) Aldopentose
25-1
PROBLEM (a) $S$ (b) $R$ (c) $S$
25-2
PROBLEM A, B, and C are the same.
25-3
PROBLEM
25-4
PROBLEM
25-5
<img class="imgSvg" id = "m6sn3qw71pq0b9da9bv" src="data:image/svg+xml;base64,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"/>


24-15 -

PROBLEM (a) L-Erythrose; $2 S, 3 S$ (b) D-Xylose; $2 R, 3 S, 4 R$ (c) D-Xylulose; $3 S, 4 R$
25-6
PROBLEM
25-7
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1197.jpg?height=269&width=446&top_left_y=1489&top_left_x=411)


24-15 -

PROBLEM
25-11
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1198.jpg?height=215&width=302&top_left_y=196&top_left_x=418)


PROBLEM -


PROBLEM -

PROBLEM
25-14
PROBLEM $\alpha$-D-Allopyranose
25-15
PROBLEM
25-16
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1198.jpg?height=204&width=608&top_left_y=1318&top_left_x=414)


PROBLEM -

PROBLEM D-Galactitol has a plane of symmetry and is a meso compound, whereas D-glucitol is chiral.
25-17
PROBLEM The -CHO end of L-gulose corresponds to the $-\mathrm{CH}_{2} \mathrm{OH}$ end of D -glucose after reduction.
25-18
PROBLEM D-Allaric acid has a symmetry plane and is a meso compound, but D-glucaric acid is chiral.
25-19
PROBLEM D-Allose and D-galactose yield meso aldaric acids; the other six D-hexoses yield optically active
25-20 aldaric acids.
PROBLEM D-Allose + D-altrose
25-21
PROBLEM L-Xylose
25-22
PROBLEM D-Xylose and D-lyxose
25-23


PROBLEM -

Diastereomers of L-threonine


PROBLEM -

PROBLEM Net positive at $\mathrm{pH}=5.3$; net negative at $\mathrm{pH}=7.3$
26-4
PROBLEM (a) Start with 3-phenylpropanoic acid: 1. $\mathrm{Br}_{2}, \mathrm{PBr}_{3} ; 2 . \mathrm{NH}_{3}$
26-5 (b) Start with 3-methylbutanoic acid: 1. $\mathrm{Br}_{2}, \mathrm{PBr}_{3} ; 2 . \mathrm{NH}_{3}$
PROBLEM
26-6
(a) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{Br}$
(b)
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(c)
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(d) $\mathrm{CH}_{3} \mathrm{SCH}_{2} \mathrm{CH}_{2} \mathrm{Br}$


PROBLEM -

PROBLEM
26-7
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1199.jpg?height=156&width=1058&top_left_y=1944&top_left_x=420)


PROBLEM -

PROBLEM Val-Tyr-Gly (VYG), Tyr-Gly-Val (YGV), Gly-Val-Tyr (GVY), Val-Gly-Tyr (VGY), Tyr-Val-Gly (YVG), Gly-
26-8 Tyr-Val (GYV)
PROBLEM
26-9
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1199.jpg?height=175&width=647&top_left_y=2208&top_left_x=414)


PROBLEM -

PROBLEM
26-11
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1200.jpg?height=220&width=798&top_left_y=405&top_left_x=406)


PROBLEM -

PROBLEM (a) Arg-Pro-Leu-Gly-Ile-Val (b) Val-Met-Trp-Asp-Val-Leu (VMWNVL)
26-15
PROBLEM This is a typical nucleophilic acyl substitution reaction, with the amine of the amino acid as the
26-16 nucleophile and tert-butyl carbonate as the leaving group. The tert-butyl carbonate then loses $\mathrm{CO}_{2}$ and gives tert-butoxide, which is protonated.
PROBLEM (1) Protect the amino group of leucine.
26-17 (2) Protect the carboxylic acid group of alanine.
(3) Couple the protected amino acids with DCC.
(4) Remove the leucine protecting group.
(5) Remove the alanine protecting group.


PROBLEM -

PROBLEM (a) Lyase (b) Hydrolase (c) Oxidoreductase
26-18