• Home
  • Textbooks
  • Organic Chemistry
  • Carboxylic Acids and Their Derivatives

Organic Chemistry

T.W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder

Chapter 17

Carboxylic Acids and Their Derivatives - all with Video Answers

Educators

Chapter Questions

13:54

Problem 1

Give an I U P A C systematic name for each of the following:

Anish Wadhwa
Anish Wadhwa
Numerade Educator
09:03

Problem 2

Which acid of each pair would you expect to be stronger?
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
06:35

Problem 3

Write structural formulas for the following:
(a) Methyl propanoate
(b) Ethyl $p$ -nitrobenzoate
(c) Dimethyl malonate
(d) $N, N$ -Dimethylbenzamide
(e) Pentanenitrile
(f) Dimethyl phthalate
(g) Dipropyl maleate
(h) $N, N$ -Dimethylformamide
(i) 2-Bromopropanoyl bromide
(i) Diethyl succinate

Kaitlyn Mchugh
Kaitlyn Mchugh
Numerade Educator
12:53

Problem 4

Show how each of the following compounds could be converted to benzoic acid:
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
08:15

Problem 5

Show how you could prepare each of the following carboxylic acids using a Grignard reagent:
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
08:57

Problem 6

(a) Which of the carboxylic acids in Practice Problem 17.5 could be prepared by a nitrile synthesis as well? (b) Which synthesis, Grignard or nitrile, would you choose to prepare
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
04:42

Problem 7

When maleic acid is heated to $200^{\circ} \mathrm{C},$ it loses water and becomes maleic anhydride. Fumaric acid, a diastercomer of malcic acid, requires a much higher temperature before it dehydrates; when it does, it also yields maleic anhydride. Provide an explanation for these observations.
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
04:22

Problem 8

Where would you expect to find the labeled oxygen if you carried out an acid-catalyzed hydrolysis of methyl benzoate in $^{18} \mathrm{O}$ -labeled water? Write a detailed mechanism to support your answer.

Kaitlyn Mchugh
Kaitlyn Mchugh
Numerade Educator
09:29

Problem 9

Esters can also be synthesized by transesterification:
In this procedure we shift the equilibrium to the right by allowing the low-boiling alcohol to distill from the reaction mixture. The mechanism for transesterification is similar to that for an acid-catalyzed esterification (or an acid-catalyzed ester hydrolysis). Write a detailed mechanism for the following transesterification:
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
11:19

Problem 10

(a) Write stereochemical formulas for compounds A-F:
1. cis-3-Methylcyclopentanol $+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{2} \mathrm{Cl} \longrightarrow \mathrm{A} \frac{\mathrm{HO}^{-}}{\text {heat }} \mathbf{B}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3}^{-}$
2. cis-3-Methylcyclopentanol $+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{C}-\mathrm{Cl} \longrightarrow \mathrm{C} \frac{\mathrm{HO}}{\text { reflux }} \mathbf{D}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CO}_{2}^{-}$
3. $(R)-2$ -Bromooctane $+\mathrm{CH}_{3} \mathrm{CO}_{2}^{-} \mathrm{Na}^{+} \longrightarrow \mathbf{E}+$ NaBr $\frac{\mathrm{HO}^{-}, \mathrm{H}_{2} \mathrm{O}}{(\text { reflux })} \mathbf{F}$
4. $(R)-2$ -Bromooctane $+\mathrm{HO}^{-} \frac{\longrightarrow}{\text { acetone }} \mathbf{F}+\mathrm{Br}^{-}$
(b) Which of the last two methods, 3 or $4,$ would you expect to give a higher yield of $F ?$ Why?

Anish Wadhwa
Anish Wadhwa
Numerade Educator
01:50

Problem 11

Base-promoted hydrolysis of methyl mesitoate occurs through an attack on the alcohol carbon instead of the acyl carbon:
(a) Can you suggest a reason that accounts for this unusual behavior? (b) Suggest an experiment with labeled compounds that would confirm this mode of attack.
FIGURES CANT COPY

Shashika Bandara
Shashika Bandara
Numerade Educator
07:01

Problem 12

What products would you obtain from acidic and basic hydrolysis of each of the following amides?
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
02:56

Problem 13

(a) Provide the reagents required to accomplish the following transformation.
(b) What product would you likely obtain if you attempted to synthesize the nitrile above by the following method?
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
05:05

Problem 14

Write structures for the products of the following reactions:
(a) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{N}=\mathrm{C}=0 \longrightarrow$
(b) $\mathrm{ClCOCl}+\mathrm{CH}_{3} \mathrm{NH}_{2}$ (excess) $\longrightarrow$
(c) Glycine $\left(\mathrm{H}_{3} \mathrm{NCH}_{2} \mathrm{CO}_{2}^{-}\right)+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OCOCl} \stackrel{\mathrm{HO}^{-}}{\longrightarrow}$
(d) Product of $(c)+H_{2}, P d \longrightarrow$
(e) Product of $(c)+H B r\left(\text { cold) }, C H_{3} C O_{2} H \longrightarrow\right.$
(f) Urea $+\mathrm{HO}^{-}, \mathrm{H}_{2} \mathrm{O},$ heat

Nicholas Sacco
Nicholas Sacco
Numerade Educator
04:06

Problem 15

Using decarboxylation reactions, outline a synthesis of each of the following from appropriate starting materials:
(a) 2 -Hexanone
(c) Cyclohexanone
(b) 2 -Methylbutanoic acid
(d) Pentanoic acid

Anish Wadhwa
Anish Wadhwa
Numerade Educator
03:16

Problem 16

(a) What factor accounts for this instability?
(b) The decomposition of a diacyl peroxide produces $\mathrm{CO}_{2} .$ How is it formed?
(c) Diacyl peroxides are often used to initiate radical reactions, such as in the polymerization of ethene. Draw the steps involved.
FIGURES CANT COPY

Lottie Adams
Lottie Adams
Numerade Educator
04:44

Problem 17

Write a structural formula for each of the following compounds:
(a) Octanoic acid
(b) Propanamide
(c) $N, N$ -Diethylhexanamide
(d) 2 -Methyl-4-hexenoic acid
(e) Butanedioic acid
(f) 1,2 -Benzenedioic acid (phthalic acid)
(g) 1,4 -Benzenedioic acid (terephthalic acid)
(h) Acetic anhydride
(i) Isobutyl propanoate
(j) Benzyl acetate
(k) Ethanoyl chloride (acetyl chloride)
(1) 2 -Methylpropanenitrile
(m) Ethyl 3-oxobutanoate (ethyl acetoacetate)
(n) Diethyl propanedioate (diethyl malonate)

Shashika Bandara
Shashika Bandara
Numerade Educator
04:49

Problem 18

Give an IUPAC systematic or common name for each of the following compounds:
FIGURES CANT COPY

Niamat Khuda
Niamat Khuda
Numerade Educator
02:13

Problem 19

Amides are weaker bases than corresponding amines. For example, t water-insoluble amines (RNH $_{2}$ ) will dissolve in dilute aqueous acids (aqueous HCI, $\left.\mathrm{H}_{2} \mathrm{SO}_{4}, \text { etc. }\right)$ by forming water-soluble alkylaminium salts (RNH $_{3}^{+} \mathrm{X}^{-}$ ). Corresponding amides (RCONHz) do not dissolve in dilute aqueous acids, however. Propose an explanation for the much lower basicity of amides when compared to amines.

Kaitlyn Mchugh
Kaitlyn Mchugh
Numerade Educator
03:36

Problem 20

While amides are much less basic than amines, they are much stronger acids. Amides have $\mathrm{p} K_{\mathrm{a}}$ values in the range $14-16$ whereas for amines, $\mathrm{p} K_{\mathrm{a}}=33-35$
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
13:18

Problem 21

What major organic product would you expect to obtain when acetyl chloride reacts with each of the following?
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
06:16

Problem 22

What major organic product would you expect to obtain when acetic
(a) $\mathrm{NH}_{3}$ (excess)
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(e) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}$ (excess)
(b) $\mathrm{H}_{2} \mathrm{O}$
$\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{AlCl}_{3}$
(f) $\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{2} \mathrm{NH}$ (excess)
FIGURE CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
06:26

Problem 23

What major organic product would you expect to obtain when succinic anhydride reacts with each of the reagents given in Problem $17.22 ?$

Anish Wadhwa
Anish Wadhwa
Numerade Educator
04:21

Problem 24

What products would you expect to obtain when ethyl propanoate reacts with each of the following?
(a) $\mathrm{H}_{3} \mathrm{O}^{+}, \mathrm{H}_{2} \mathrm{O}$
(b) $\mathrm{HO}^{-}, \mathrm{H}_{2} \mathrm{O}$
(c) 1 -Octanol, HCl
(d) $\mathrm{CH}_{3} \mathrm{NH}_{2}$
(e) LiAIH $_{4},$ then $\mathrm{H}_{2} \mathrm{O}$
(f) Excess $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr},$ then $\mathrm{H}_{2} \mathrm{O}, \mathrm{NH}_{4} \mathrm{Cl}$

Kaitlyn Mchugh
Kaitlyn Mchugh
Numerade Educator
02:25

Problem 25

What products would you expect to obtain when propanamide reacts with each of the following?
(a) $\mathrm{H}_{3} \mathrm{O}^{+}, \mathrm{H}_{2} \mathrm{O}$
(b) $\mathrm{HO}^{-}, \mathrm{H}_{2} \mathrm{O}$
(c) $\mathrm{P}_{4} \mathrm{O}_{10}$ and heat

Anish Wadhwa
Anish Wadhwa
Numerade Educator
07:44

Problem 26

What products would you expect to obtain when each of the following compounds is heated?
(a) 4 -Hydroxybutanoicacid
(b) 3 -Hydroxybutanoic acid
(c) 2-Hydroxybutanoic acid
(d) Glutaric acid
FIGURES CANT COPY

George Bennett
George Bennett
Numerade Educator
06:53

Problem 27

Write structural formulas for the major organic products from each of the following reactions.
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
09:18

Problem 28

Indicate reagents that would accomplish each of following transformations. More than one reaction may be necessary in some cases.
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
05:10

Problem 29

Write structural formulas for the major organic products from each of the following reactions.
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
06:28

Problem 30

Write structural formulas for the major organic products from each of the following reactions.
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
05:12

Problem 31

Write detailed mechanisms for the acidic and basic hydrolysis of propanamide.

Kaitlyn Mchugh
Kaitlyn Mchugh
Numerade Educator
11:12

Problem 32

Provide a detailed mechanism for each of the following reactions..
FIGURES CANT COPY

Zubair Abdulla
Zubair Abdulla
Numerade Educator
02:09

Problem 33

On heating, cis-4-hydroxycyclohexanecarboxylic acid forms a lactone but trans-4-hydroxycyclohexanecarboxylic acid does not. Explain.

Anish Wadhwa
Anish Wadhwa
Numerade Educator
04:37

Problem 34

Show how $p$ -chlorotoluene could be converted to each of the following:
FIGURES CANT COPY

Debasish Das
Debasish Das
Numerade Educator
03:52

Problem 35

Indicate the reagents needed for each of the following syntheses. More than one step may be needed.
FIGURES CANT COPY

Anish Wadhwa
Anish Wadhwa
Numerade Educator
04:41

Problem 36

Show how pentanoic acid can be prepared from each of the following:
(a) 1 -Pentanol
(b) 1 -Bromobutane (two ways)
(c) 5 -Decene
(d) Pentanal

Anish Wadhwa
Anish Wadhwa
Numerade Educator
02:33

Problem 37

The active ingredient of the insect repellent Off is $N, N$ -diethyl-m-toluamide, $m-\mathrm{CH}_{3} \mathrm{C}_{6} \mathrm{H}_{4} \mathrm{CON}\left(\mathrm{CH}_{2} \mathrm{CH}_{3}\right)_{2} .$ Outline a synthesis of this compound starting with 3 -methylbenzoic acid ( $m$ -toluic acid).

Anish Wadhwa
Anish Wadhwa
Numerade Educator
01:15

Problem 38

Starting with benzene and succinic anhydride and using any other needed reagents, outline a synthesis of 1 -phenylnaphthalene.

Lottie Adams
Lottie Adams
Numerade Educator
09:13

Problem 39

Starting with cither $c i$ - or trans -HO,C $-\mathrm{CH}=\mathrm{CH}-\mathrm{CO}_{2} \mathrm{H}$ (i.e., cither maleic or fumaric acid) and using any other needed compounds, outline syntheses of each of the following:
FIGURES CANT COPY

Ronald Prasad
Ronald Prasad
Numerade Educator
08:40

Problem 40

Give stereochemical formulas for compounds $\mathbf{A}-\mathbf{Q}$
(a) $(R)-(-)-2-$ Butanol $\frac{\text { ctotouenessurtony }}{\text { pridine }} \mathbf{A} \stackrel{-\mathrm{C}=\mathrm{N}}{\longrightarrow} \mathbf{B}\left(\mathrm{C}_{5} \mathrm{H}_{\mathrm{G}} \mathrm{N}\right) \frac{\mathrm{H}_{2} \mathrm{SO}_{4}}{\mathrm{H}_{2} \mathrm{O}}(+)-\mathbf{C}\left(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}_{2}\right) \frac{(1) \mathrm{L}\left(\mathrm{AH}_{4}-\right.}{12) \mathrm{H}_{2} \mathrm{O}}(-)-\mathrm{D}\left(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\right)$
(b) $(R)-(-)-2-$ Butanol $\frac{\mathrm{PB} \mathrm{B}_{3}}{\text { pridine }} \mathbf{E}\left(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Br}\right) \stackrel{-\mathrm{C}=\mathrm{N}}{\longrightarrow} \mathrm{F}\left(\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{N}\right) \frac{\mathrm{H}_{2} \mathrm{SO}_{4}}{\mathrm{H}_{2} \mathrm{O}}(-)-\mathrm{C}\left(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}_{2}\right) \frac{(1) \mathrm{L}_{2} \mathrm{A}_{4}-}{(2) \mathrm{H}_{2} \mathrm{O}}(+)-\mathrm{D}\left(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\right)$
(c) $\mathrm{A} \stackrel{\mathrm{CH}_{3} \mathrm{CO}_{2}^{-}}{\longrightarrow} \mathrm{G}\left(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{2}\right) \stackrel{\mathrm{HO}^{-}}{\longrightarrow}(+)-\mathrm{H}\left(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\right)+\mathrm{CH}_{3} \mathrm{CO}_{2}^{-}$
(d) $(-)-\mathbf{D} \stackrel{\mathrm{PBr}_{3}}{\longrightarrow} \mathrm{J}\left(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{Br}\right) \frac{\mathrm{Mg}}{\mathrm{E}_{2} \mathrm{O}} \mathbf{K}\left(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{MgBr}\right) \frac{(1) \mathrm{CO}_{2}}{(2) \mathrm{H}_{3} \mathrm{O}^{+}} \mathbf{L}\left(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{2}\right)$
FIGURES CANT COPY

George Bennett
George Bennett
Numerade Educator
01:01

Problem 41

(R)-(+)-Glyceraldehyde can be transformed into (t)-malic acid by the following synthetic route. Give stereochemical structures for the products of each step.
(R)-(+)-Glyceraldehyde $\frac{86}{\text { expation }}$ (-)-slycric acid $\stackrel{\text { PEG. }}{\text { - }}$ (-)-3-bromo-2-hydroxypropanoic acid $\frac{\text { NacN }}{\text { - }} \mathrm{C}_{4}$ H $_{5}$ NO $_{3}$ $\frac{\text { Ho }}{\text { heat }}$. (t)-malic acid

Narayan Hari
Narayan Hari
Numerade Educator
View

Problem 42

(R)-(+)-Glyceraldehyde can also be transformed into (-)-malic acid. This synthesis begins with the conversion of $(R)-(+)$ -glyccraldehyde into (-)-tartaric acid, as shown in Problem 17.40 , parts ( $e$ ) and (g). Then (-)-tartaric acid is allowed to react with phosphorus tribromide in order to replace one alcoholic $-$ OH group with $-$ Br. This step takes place with inversion of configuration at the carbon that undergoes attack. Treating the product of this reaction with dimethy sulfide produces (-)-malic acid. (a) Outline all steps in this synthesis by writing stereochemical structures for each intermediate. (b) The step in which (-)-tartaric acid is treated with phosphorus tribromide produces only one stereoisomer, even though there are two replaceable - OH groups. How is this possible? (c) Suppose that the step in which (-)-tartaric acid is treated with phosphorus tribromide had taken place with "mixed" stereochemistry, that is, with both inversion and retention at the carbon under attack. How many stereoisomers would have been produced? (d) What difference would this have made to the overall outcome of the synthesis?

Lainey Roebuck
Lainey Roebuck
Numerade Educator
02:39

Problem 43

The IR and 'H NMR spectra of phenacetin $\left(\mathrm{C}_{10} \mathrm{H}_{13} \mathrm{NO}_{2}\right)$ are given in Fig. 17.7. Phenacetin is an analgesic and antipyretic compound and was the P of A-P-C tablets (aspirin-phenacetin-caffeine). (Because of its toxicity, phenacetin is no longer used medically.) When phenacetin is heated with aqueous sodium hydroxide, it yields phenetidine (C $_{8} \mathrm{H}_{11}$ NO) and sodium acctate. Propose structures for phenacetin and phenetidine.
FIGURES CANT COPY

Nicole Krahulik
Nicole Krahulik
Numerade Educator
10:17

Problem 44

Give the $(R, S)$ designation for each compound given as an answer to Practice Problem 5.29
(a) $\mathrm{C}_{8} \mathrm{H}_{14} \mathrm{O}_{4}$ $^{1} \mathrm{H} \mathrm{NMR}$ Spectrum
Triplet $\delta 1.2(6 \mathrm{H})$
Singlet $\delta 2.5(4 \mathrm{H})$
Quartet $\quad \delta 4.1(4 \mathrm{H})$ IR Spectrum $1740 \mathrm{cm}^{-1}$
(b) $\mathrm{C}_{11} \mathrm{H}_{14} \mathrm{O}_{2}$
$^{1} \mathrm{H} \mathrm{NMR}$ Spectrum
Doublet $\quad \delta 1.0(6 \mathrm{H})$
Multiplet $\quad \delta 2.1(1 \mathrm{H})$
Doublet $\delta 4.1(2 \mathrm{H})$
Multiplet $\quad \delta 7.8(5 \mathrm{H})$ IR Spectrum $1720 \mathrm{cm}^{-1}$
(c) $\mathrm{C}_{10} \mathrm{H}_{12} \mathrm{O}_{2}$
$^{1} \mathrm{H} \mathrm{NMR}$ Spectrum
Triplet $\delta 1.2(3 \mathrm{H})$
Singlet $\delta 3.5(2 \mathrm{H})$
Quartet $\delta 4.1(2 \mathrm{H})$
Multiplet $\quad \delta 7.3(5 \mathrm{H})$
IR Spectrum $1740 \mathrm{cm}^{-1}$
(d) $\mathrm{C}_{2} \mathrm{H}_{2} \mathrm{Cl}_{2} \mathrm{O}_{2}$
'H NMR Spectrum
singlet $\delta 6.0$
Singlet $\delta 11.70$
IR Spectrum
Broad peak $2500-2700 \mathrm{cm}^{-1}$
$1705 \mathrm{cm}^{-1}$
(e) $\mathrm{C}_{4} \mathrm{H}_{7} \mathrm{ClO}_{2}$
'H NMR Spectrum
Triplet $\delta 1.3$
singlet $\delta 4.0$
Quartet $\delta 4.2$
IR Spectrum $1745 \mathrm{cm}^{-1}$

Ian Kaigh
Ian Kaigh
Numerade Educator
06:36

Problem 45

Compound $\mathbf{Y}\left(\mathrm{C}_{8} \mathrm{H}_{4} \mathrm{O}_{3}\right)$ dissolves slowly when warmed with aqueous sodium bicarbonate. The IR spectrum of $\mathbf{Y}$ has strong peaks at 1779 and at $1854 \mathrm{cm}^{-1}$. The broadband proton-decoupled ' $^{13}$ C spectrum of $Y$ exhibits signals at $\delta 125(\mathrm{CH}), 130(\mathrm{C}), 136(\mathrm{CH}),$ and 162 (C). Acidification of the bicarbonate solution of $\mathbf{Y}$ gave compound $\mathbf{Z}$. The proton-decoupled ' $^{13} \mathrm{C}$ NMR spectrum of $\mathbf{Z}$ showed four signals. When Y was warmed in ethanol, compound AA was produced. The '3C NMR spectrum of AA displayed 10 signals. Propose structures for $\mathbf{Y}, \mathbf{Z}$ and $\mathbf{A A}$

Ian Kaigh
Ian Kaigh
Numerade Educator
06:35

Problem 46

Cantharidin is a powerful vesicant that can be isolated from dried beetles (Cantharis vesicatoria, or the "Spanish fly"). Outlined here are some of the key steps of a stereospecific synthesis of cantharidin reported by Gilbert Stork (Columbia University). Supply the missing reagents ( $a$ )-(i).
FIGURES CANT COPY

Susan Hallstrom
Susan Hallstrom
Numerade Educator
02:11

Problem 47

For each of the following questions, please provide a route that could reasonably be expected to convert the starting material into the final product. In each case, more than one reaction is required, and reactions you have learned in previous chapters may be needed to solve the problem.
FIGURES CANT COPY

Lottie Adams
Lottie Adams
Numerade Educator
02:29

Problem 48

For each of the following, identify the product (represented by $\mathbf{A}, \mathbf{B}, \mathbf{C},$ and $\mathbf{D}$ ) that would be formed through the indicated sequence of steps from the given starting material.
FIGURES CANT COPY

Lottie Adams
Lottie Adams
Numerade Educator
02:36

Problem 49

Working backwards, deduce the starting material that led to the indicated product through the defined reactions.
FIGURES CANT COPY

Lottie Adams
Lottie Adams
Numerade Educator
01:07

Problem 50

Ketene, $\mathrm{H}_{2} \mathrm{C}=\mathrm{C}=0,$ is an important industrial chemical. Predict the products that would be formed when ketene reacts with
(a) cthanol, (b) acetic acid, and (c) ethylamine. (Hint: Markovnikov addition occurs.)

Mishal Gul
Mishal Gul
Numerade Educator
02:44

Problem 51

Two unsymmetrical anhydrides react with ethylamine as drawn below. Explain the factors that might account for the formation of the products in each reaction.
FIGURES CANT COPY

Zubair Abdulla
Zubair Abdulla
Numerade Educator
06:17

Problem 52

Starting with 1 -naphthol, suggest an alternative synthesis of the insecticide Sevin to the one given in Section $17.9 \mathrm{A}$

Shazia Naz
Shazia Naz
Numerade Educator
02:28

Problem 53

Suggest a synthesis of ibuprofen (Section 5.11) from benzene, employing chloromethylation as one step. Chloromethylation is a special case of the Friedel-Crafts reaction in which a mixture of HCHO and HCl, in the presence of ZnCle, introduces a $-\mathrm{CH}_{2} \mathrm{Cl}$ group into an aromatic ring.

Ian Kaigh
Ian Kaigh
Numerade Educator
03:00

Problem 54

An alternative synthesis of ibuprofen is given below. Supply the structural formulas for compounds A-D:
FIGURES CANT COPY

Katie Miller
Katie Miller
Numerade Educator
05:29

Problem 55

As a method for the synthesis of cinnamaldehyde (3-phenyl-2-propenal), a chemist treated 3-phenyl-2-propen-1-ol with $\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}$ in sulfuric acid. The product obtained from the reaction gave a signal at $\delta$ i64.5 in its $13 \mathrm{C}$ NMR spectrum. Alternatively, when the chemist treated 3 -phenyl-2-propen-1-ol with $\mathrm{PCC}$ in $\mathrm{CH}_{2} \mathrm{Cl}_{2}$, the $^{3}$ and of of the product displayed a signal at $\delta 193.8$. (All other signals in the spectra of both compounds appeared at similar chemical shifts.) (a) Which reaction produced cinnamaldehyde?
(b) What was the other product?

Susan Hallstrom
Susan Hallstrom
Numerade Educator