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Schaum's Outline of Organic Chemistry

George Hademenos, George Hademenos

Chapter 16

CARBOXYLIC ACIDS AND THEIR DERIVATIVES - all with Video Answers

Educators

Chapter Questions

Problem 1

CAN'T COPY

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02:07

Problem 1

Prepare $n$-hexyl chloride from $n$-butylmalonic ester.

Madeline Currie
Madeline Currie
Numerade Educator
03:41

Problem 1

(a) Suggest a mechanism for a ready decarboxylation of malonic acid, $\mathrm{HOOCCH}_2 \mathrm{COOH}_{\text {, that }}$ proceeds through an activated, intramolecular $\mathrm{H}$-bonded, intermediate complex. (b) Give the decarboxylation products of (i) oxalic acid, $\mathrm{HOOC}-\mathrm{COOH}$, and (ii) pyruvic acid, $\mathrm{CH}_3 \mathrm{COCOOH}$.

Ian Kaigh
Ian Kaigh
Numerade Educator
06:38

Problem 1

The $K_2$ for fumaric acid (trans-butaenedioic acid) is greater than that for maleic acid, the cis isomer. Explain by $\mathrm{H}$-bonding.

Yogesh R
Yogesh R
Numerade Educator
01:19

Problem 2

Name the following aromatic carboxylic acids.

(a)CAN'T COPY
(b)CAN'T COPY
(c)CAN'T COPY
(d)CAN'T COPY

Lottie Adams
Lottie Adams
Numerade Educator
04:07

Problem 3

Account for the following physical properties of carboxylic acids. (a) Only RCOOH's with five or fewer C's are soluble in water, but many with six or more C's dissolve in alcohols. (b) Acetic acid in the vapor state has a molecular weight of 120 not 60 . (c) Their boiling and melting points are higher than those of corresponding alcohols.

Tom Rutherford
Tom Rutherford
Numerade Educator
05:26

Problem 3

Use the mechanism of esterification to explain the lower rates of both esterification and hydrolysis of esters when the alcohol, the acid, or both have branched substituent groups.

Tom Rutherford
Tom Rutherford
Numerade Educator

Problem 3

Give the structural formula and name for the product formed when $1 \mathrm{~mol}$ of succinic anhydride, the cyclic anhydride of succinic acid (Problem 16.22), reacts with (a) $1 \mathrm{~mol}$ of $\mathrm{CH}_3 \mathrm{OH} ;\left(\right.$ b) $2 \mathrm{~mol}$ of $\mathrm{NH}_3$ and $(c$ ) $1 \mathrm{~mol}$ of $\mathrm{C}_6 \mathrm{H}_6$ with $\mathrm{AlCl}_3$.

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04:37

Problem 4

Write resonance structures for the $\mathrm{COOH}$ group and show how these and orbital hybridization account for: (a) polarity and dipole moments (1.7-1.9D) of carboxylic acids; $(b)$ their low reactivity toward nucleophilic additions, as compared to carbonyl compounds.

Anish Wadhwa
Anish Wadhwa
Numerade Educator
02:25

Problem 5

Prepare $(a)$ tosylamide $\left(\mathrm{T}_{\mathrm{s}}=t o s y \mathrm{l}=p-\mathrm{CH}_3 \mathrm{C}_6 \mathrm{H}_4 \mathrm{SO}_2-\right.$ ) from toluene, (b) PhCOOH from $\mathrm{PhSO}_2 \mathrm{Cl}$, (c) o-methylthiophenol from $\mathrm{PhCH}_3$.

Raghvendra Singh
Raghvendra Singh
Numerade Educator
02:09

Problem 5

What products are formed when 1 mol of urea reacts with $(a) 1 \mathrm{~mol},(b)$ a second mol of methyl acetate (or acetyl chloride)?

Lottie Adams
Lottie Adams
Numerade Educator
02:48

Problem 5

Write structures for compounds (A) through (C) in the synthesis of saccharin.

Nicholas Sacco
Nicholas Sacco
Numerade Educator
01:23

Problem 5

Write formulas for each of the following: (a) phenylacetic acid, (b) phenylethanoic acid, (c) 2 methylpropenoic acid, $(d)(E)$-butenedioic acid, $(e)$ ethanedioic acid, $(f)$ 3-methylbenzenecarboxylic acid.

Vasu Makani
Vasu Makani
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06:03

Problem 5

Name the following compounds:

Jennifer Hudspeth
Jennifer Hudspeth
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00:56

Problem 5

Name the following derivatives:
(a)CAN'T COPY
(b)CAN'T COPY
(c)CAN'T COPY
(d)CAN'T COPY
(e)CAN'T COPY
(f)CAN'T COPY
(g)CAN'T COPY
(h)CAN'T COPY

Linh Vu
Linh Vu
Numerade Educator
09:21

Problem 6

Use ethanol as the only organic compound to prepare (a) $\mathrm{HOCH}_2 \mathrm{COOH}$, (b) $\mathrm{CH}_3 \mathrm{CHOHCOOH}$.

Katie Miller
Katie Miller
Numerade Educator
02:42

Problem 6

Give structural formulas for the following acid derivatives: $(a)$ propionitrile, $(b)$ isopropyl-2fluorobutanoate, (c) 3-phenylhexanoyl chloride, (d) 3-chloropropyl benzoate.

Sima Sarker
Sima Sarker
Numerade Educator
01:47

Problem 7

Account for the fact that on oxidative cleavage all substituted alkynes give carboxylic acids, whereas some alkenes give ketones.

Dalton Hilovsky
Dalton Hilovsky
Numerade Educator
01:11

Problem 8

(a) Why isn't 2-naphthoic acid made from 2-chloronaphthalene? $(b)$ How is 2-naphthoic acid prepared in a haloform reaction?

Tom Rutherford
Tom Rutherford
Numerade Educator
00:32

Problem 9

Prepare the following acids from alkyl halides or dihalides of fewer $\mathrm{C}$ 's. (a) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{COOH}$, (b) $\left(\mathrm{CH}_3\right)_3 \mathrm{CCOOH}$, (c) $\mathrm{HOCH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{COOH}$, (d) $\mathrm{HOOCCH} \mathrm{CH}_2 \mathrm{COOH}$ (succinic acid).

Raghvendra Singh
Raghvendra Singh
Numerade Educator
03:01

Problem 10

Use the concept of charge delocalization by extended $\pi$ bonding (resonance) to explain why (a) $\mathrm{RCOOH}\left(\mathrm{p} K_a \approx 5\right)$ is more acidic than $\mathrm{ROH}\left(\mathrm{p} K_a \approx 15\right)$, and $(b)$ peroxy acids, $\mathrm{RCOOH}$, are much weaker than $\mathrm{RCOOH}$.
<smiles>[CH][CH]</smiles>

David Taylor
David Taylor
Numerade Educator
06:24

Problem 11

Use the inductive effect (Section 3.11) to account for the following differences in acidity, (a) $\mathrm{ClCH}_2 \mathrm{COOH}>\mathrm{CH}_3 \mathrm{COOH}$, (b) $\mathrm{FCH}_2 \mathrm{COOH}>\mathrm{ClCH}_2 \mathrm{COOH}$, (c) $\mathrm{ClCH}_2 \mathrm{COOH}>\mathrm{ClCH}_2 \mathrm{CH}_2 \mathrm{COOH}$, (d) $\mathrm{Me}_3 \mathrm{CCH}_2 \mathrm{COOH}>\mathrm{Me}_3 \mathrm{SiCH}_2 \mathrm{COOH},(e) \mathrm{Cl}_2 \mathrm{CHCOOH}>\mathrm{ClCH}_2 \mathrm{COOH}$.

Nadir Iqbal
Nadir Iqbal
Numerade Educator
01:31

Problem 12

Explain why highly branched carboxylic acids such as
<smiles>CC(C)(C)C(C)(C(=O)O)C(C)(C)C</smiles>
are less acidic than unbranched acids.

Ly Tran
Ly Tran
Numerade Educator
04:00

Problem 13

Although $p$-hydroxybenzoic acid is less acidic than benzoic acid, salicyclic ( $o$-hydroxybenzoic) acid $\left(K_a=105 \times 10^{-5}\right)$ is 15 times more acidic than benzoic acid. Explain.

Ian Kaigh
Ian Kaigh
Numerade Educator
05:26

Problem 15

Give the mechanism for the acid-catalyzed esterification of $\mathrm{RCOOH}$ with $\mathrm{R}^{\prime} \mathrm{OH}$.

Tom Rutherford
Tom Rutherford
Numerade Educator
01:21

Problem 16

Use ethanol to prepare $\mathrm{CH}_3 \mathrm{COOC}_2 \mathrm{H}_5$, an important commercial solvent.

Vasu Makani
Vasu Makani
Numerade Educator
03:26

Problem 16

Prepare malonic acid (propanedioic acid, $\mathrm{HOOC}-\mathrm{CH}_2-\mathrm{COOH}$ ) from $\mathrm{CH}_3 \mathrm{COOH}$.

Isaac Huidobro
Isaac Huidobro
Numerade Educator
02:04

Problem 17

The pain reliever acetaminophen is produced by reacting 4-aminophenol with acetic anhydride. Outline a synthesis of acetaminophen from 4-aminophenol including any needed inorganic reagents.

Madeline Currie
Madeline Currie
Numerade Educator

Problem 20

Suggest a typical free-radical mechanism for the Hunsdiecker reaction which requires the initial formation of an acyl hypobromite,
<smiles>[R]C(=O)O[Bi]Br</smiles>
from the $\mathrm{Ag}^{+}$salt and $\mathrm{Br}_2$.

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03:09

Problem 21

(a) Account for the fact that $\mathrm{ArCOOH}$, with a strongly activating substituent ortho or para to $\mathrm{COOH}$, loses $\mathrm{CO}_2$ during attempted electrophilic substitution. (b) Write the equation for the reaction of $p$ aminobenzoic acid and $\mathrm{Br}_2$.

Mak Smith
Mak Smith
Numerade Educator
06:43

Problem 22

Compare the products formed on heating the following dicarboxylic acids: $(a)$ succinic acid, (b) glutaric acid (1,5-pentanedioic acid), (c) longer-chain $\mathrm{HOOC}\left(\mathrm{CH}_2\right)_n \mathrm{COOH}$.

Yogesh R
Yogesh R
Numerade Educator
03:14

Problem 23

Show steps in the following syntheses, using any needed inorganic reagents:

Zubair Abdulla
Zubair Abdulla
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12:25

Problem 24

Write the structure for the lactone formed on heating in the presence of acid $(a) \gamma$-hydroxybutyric acid, (b) $\delta$-hydroxyvaleric acid.

Tom Rutherford
Tom Rutherford
Numerade Educator
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Problem 25

(a) When heated, $2 \mathrm{~mol}$ of an $\alpha$-hydroxyacid $(n=0)$ lose $2 \mathrm{~mol}$ of $\mathrm{H}_2 \mathrm{O}$ to give a cyclic diester (a lactide). Give the structural formulas for two diastereomers obtained from lactic acid, $\mathrm{CH}_3 \mathrm{CHOHCOOH}$, and select the diastereomer which is not resolvable. (b) Synthesize lactic acid from $\mathrm{CH}_3 \mathrm{CHO}$.

Bridger Johnston
Bridger Johnston
Numerade Educator
05:11

Problem 27

What is the product when each of the following compounds is reacted with aqueous base $(\mathrm{NaOH})$ ?
(a) 2-bromobutanoic acid, (b) 3-bromobutanoic acid, (c) 4-bromobutanoic acid, (d) 5-bromopentanoic acid. (In
(a) and (b) the initially formed salt is acidified.)

Crystal Wang
Crystal Wang
Numerade Educator
01:30

Problem 28

(a) Give the mechanism for the reaction of $\mathrm{RCOCl}$ with $\mathrm{Nu}:-$. (b) Compare, and explain the difference in the reactivities of $\mathrm{RCl}$ and $\mathrm{RCOCl}$ with $\mathrm{Nu}^{--}$. (c) What is the essential difference between nucleophilic attack on $\mathrm{C}=\mathrm{O}$ of a ketone or aldehyde and of an acid derivative?

Nicole Krahulik
Nicole Krahulik
Numerade Educator
00:25

Problem 29

Account for the relative reactivities of $\mathrm{RCOG}$ with nucleophiles: $\mathrm{RCOX}>\left(\mathrm{RCO}_2\right)_2 \mathrm{O}>$ $\mathrm{RCOOR}^{\prime}>\mathrm{RCONH}_2$.

Hunza Gilgit
Hunza Gilgit
Numerade Educator
02:13

Problem 30

Place acyl azides, $\mathrm{R}-\mathrm{C}-\mathrm{N}_3$, in the order of reactivities, if for hydrazoic acid, $\mathrm{HN}_3$, $K_a=2.6 \times 10^{-5}$. Recall that for $\mathrm{CH}_3 \mathrm{COOH}, K_a=1.8 \times 10^{-5}$.

Anand Jangid
Anand Jangid
Numerade Educator
06:54

Problem 31

Use the Hammond principle (Problem 11.8) to explain why strong bases such as $\mathrm{OR}^{-}$(from esters) and $\mathrm{NH}_2^{-}$(from amides) can be leaving groups in nucleophilic transacylations.

Dr. Satish Ingale
Dr. Satish Ingale
Numerade Educator
01:28

Problem 32

Outline a mechansim for hydrolysis of acid derivaties with $(a) \mathrm{H}_3 \mathrm{O}^{+},(b) \mathrm{NaOH}$.

David Collins
David Collins
Numerade Educator
00:56

Problem 33

Does each of the following reactions take place easily? Explain.

(a) $\mathrm{CH}_3 \mathrm{COCl}+\mathrm{H}_2 \mathrm{O} \longrightarrow \mathrm{CH}_3 \mathrm{COOH}+\mathrm{HCl}$
(b) $\mathrm{CH}_3 \mathrm{COOH}+\mathrm{NH}_3 \longrightarrow \mathrm{CH}_3 \mathrm{CONH}_2+\mathrm{H}_2 \mathrm{O}$
(c) $\left(\mathrm{CH}_3 \mathrm{CO}\right)_2 \mathrm{O}+\mathrm{NaOH} \longrightarrow \mathrm{CH}_3 \mathrm{COOH}+\mathrm{CH}_3 \mathrm{COO}^{-} \mathrm{Na}^{+}$
(d) $\mathrm{CH}_3 \mathrm{COBr}+\mathrm{C}_2 \mathrm{H}_5 \mathrm{OH} \longrightarrow \mathrm{CH}_3 \mathrm{COOC}_2 \mathrm{H}_5+\mathrm{HBr}$
(e) $\mathrm{CH}_3 \mathrm{CONH}_2+\mathrm{NaOH} \longrightarrow \mathrm{CH}_3 \mathrm{COO}^{-} \mathrm{Na}^{+}+\mathrm{NH}_3$
(f) $\mathrm{CH}_3 \mathrm{COOCH}_3+\mathrm{Br}^{-} \longrightarrow \mathrm{CH}_3 \mathrm{COBr}+{ }^{-} \mathrm{OCH}_3$

Dr. Satish Ingale
Dr. Satish Ingale
Numerade Educator

Problem 34

Give the structure and name of the principal product formed when propionyl chloride reacts with: (a) $\mathrm{H}_2 \mathrm{O}$, (b) $\mathrm{C}_2 \mathrm{H}_5 \mathrm{OH}$, (c) $\mathrm{NH}_3,($ d $) \mathrm{C}_6 \mathrm{H}_6\left(\mathrm{AlCl}_3\right)$, (e) $\left(n-\mathrm{C}_3 \mathrm{H}_7\right)_2 \mathrm{CuLi},(f)$ aq. NaOH, (g) LiAl $\left(\mathrm{O}-t-\mathrm{C}_4 \mathrm{H}_9\right)_3,(h)$ $\mathrm{H}_2 \mathrm{NOH},(i) \mathrm{CH}_3 \mathrm{NH}_2,\left(\right.$ j) $\mathrm{Na}_2 \mathrm{O}_2$ (sodium peroxide).

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01:02

Problem 35

Give the products formed when acetic anhydride reacts with $(a) \mathrm{H}_2 \mathrm{O}$, (b) $\mathrm{NH}_3,(c) \mathrm{C}_2 \mathrm{H}_5 \mathrm{OH}$, (d) $\mathrm{C}_6 \mathrm{H}_6$ with $\mathrm{AlCl}_3$.

Narayan Hari
Narayan Hari
Numerade Educator
05:26

Problem 38

Write mechanisms for the reactions of $\mathrm{RCOOR}^{\prime}$ with (a) aqueous $\mathrm{OH}^{-}$to form $\mathrm{RCOO}^{-}$and $\mathrm{R}^{\prime} \mathrm{OH}$ (saponification), (b) $\mathrm{NH}_3$ to form $\mathrm{RCONH}_2$, (c) $\mathrm{R}^{\prime \prime} \mathrm{OH}$ in acid, $\mathrm{HA}$, to form a new ester $\mathrm{RCOOR}^{\prime \prime}$ (transesterification; Section 16.6).

Tom Rutherford
Tom Rutherford
Numerade Educator
07:25

Problem 39

Assign numbers from 1 for LEAST to 4 for MOST to show relative rates of alkaline hydrolysis of compounds I through IV and point out the factors determining the rates.

Preeti Kumari
Preeti Kumari
Numerade Educator
05:43

Problem 40

Acid-catalyzed hydrolysis with $\mathrm{H}_2{ }^{18} \mathrm{O}$ of an ester of an optically active $3^{\circ}$ alcohol, $R_{C O O C}{ }^* R^{\prime} R^{\prime \prime} R^{\prime \prime \prime}$, yields the partially racemic alcohol containing ${ }^{18} O, R^{\prime} R^{\prime \prime} R^{\prime \prime \prime} C^{18} O H$. Similar hydrolyses of esters of $2^{\circ}$ chiral alcohols, RCOOC ${ }^* \mathrm{HR}^{\prime} \mathrm{R}^{\prime \prime}$, produce no change in the optical activity of the alcohol, and ${ }^{18} \mathrm{O}$ is found in $\mathrm{RC}^{18} \mathrm{O}_2 \mathrm{H}$. Explain these observations.

Nima Gharibi
Nima Gharibi
Numerade Educator
08:02

Problem 41

Write structures of the organic products for the following reactions:
(a) (R) $-\mathrm{CH}_3 \mathrm{COOCH}\left(\mathrm{CH}_3\right) \mathrm{CH}_2 \mathrm{CH}_3+\mathrm{H}_2 \mathrm{O} \stackrel{\mathrm{NaOH}}{-}$
(b) (R) $-\mathrm{CH}_3 \mathrm{COOCH}\left(\mathrm{CH}_3\right) \mathrm{CH}_2 \mathrm{CH}_3+\mathrm{H}_3 \mathrm{O}^{+} \longrightarrow$
(c) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{COOC}_2 \mathrm{H}_5+\mathrm{NH}_3 \longrightarrow$
(d) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{COOC}_2 \mathrm{H}_5+n-\mathrm{C}_4 \mathrm{H}_9 \mathrm{OH} \stackrel{\mathrm{H}^{+}}{\longrightarrow}$
(e) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{COOC}_2 \mathrm{H}_5+\mathrm{LiAlH}_4 \longrightarrow$
(f)
<smiles>C[14CH2]O[14CH2]c1ccccc1</smiles>

Nicholas Sacco
Nicholas Sacco
Numerade Educator
06:31

Problem 42

Supply a structural formula for the alcohol formed from
(a) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{COOCH}_3+2 \mathrm{C}_3 \mathrm{H}_7 \mathrm{MgBr}$
(b) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{COOCH}_3+2 \mathrm{C}_6 \mathrm{H}_5 \mathrm{MgBr}$

Colton Wang
Colton Wang
Numerade Educator
01:01

Problem 43

Methyl esters can be prepared on a small scale from $\mathrm{RCOOH}$ and $\mathrm{CH}_2 \mathrm{~N}_2$. Suggest a mechanism involving $\mathrm{S}_{\mathrm{N}} 2$ displacement of $\mathrm{N}_2$.

Narayan Hari
Narayan Hari
Numerade Educator
08:29

Problem 44

In living cells, alcohols are converted to acetate esters (acetylated) by the thiol ester $\mathrm{CH}_3 \mathrm{COS}-(\mathrm{CoA})$, acetyl coenzyme $\mathrm{A}$. CoA is an abbreviation for a very complex piece. Illustrate this reaction using glycerol-1-phosphate.

Tom Rutherford
Tom Rutherford
Numerade Educator
00:34

Problem 45

(a) Write a formula for a fat (found in butter) of butanoic acid. (b) Alkaline hydrolysis of a fat of a high-molecular-weight acid gives a carboxylate salt (a soap). Write the equation for the reactions of the fat of palmitic acid, $n-\mathrm{C}_{15} \mathrm{H}_3 \mathrm{COOH}$, with aqueous $\mathrm{NaOH}$.

David Collins
David Collins
Numerade Educator
01:16

Problem 46

Two isomeric triglycerides are hydrolyzed to $1 \mathrm{~mol} \mathrm{of} \mathrm{C}_{17} \mathrm{H}_{33} \mathrm{COOH}$ (A) and $2 \mathrm{~mol}$ of $\mathrm{C}_{17} \mathrm{H}_{35} \mathrm{COOH}$ (B). Reduction of B yields $n$-stearyl alcohol, $\mathrm{CH}_3\left(\mathrm{CH}_2\right)_{16} \mathrm{CH}_2 \mathrm{OH}$. Compound $\mathrm{A}$ adds $1 \mathrm{~mol}$ of $\mathrm{H}_2$ to give $\mathrm{B}$ and is cleaved with $\mathrm{O}_3$ to give nonanal, $\mathrm{CH}_3\left(\mathrm{CH}_2\right)_7 \mathrm{CH}=\mathrm{O}$, and 9-oxononoic acid, $\mathrm{O}=\mathrm{CH}\left(\mathrm{CH}_2\right)_7 \mathrm{COOH}$. What are the structures of the isomeric glycerides?

Raghvendra Singh
Raghvendra Singh
Numerade Educator
01:09

Problem 47

Use the concepts of charge delocalization and resonance to account for the acidity of imides. (They dissolve in $\mathrm{NaOH}$.)

Lizabeth Tumminello
Lizabeth Tumminello
Numerade Educator
01:15

Problem 48

A carboxylic acid has $\mathrm{GMW}=118$, and $169.6 \mathrm{~mL}$ of $1.000 \mathrm{~N} \mathrm{KOH}$ neutralizes $10.0 \mathrm{~g}$ of the acid. When heated, $1 \mathrm{~mol}$ of this acid loses $1 \mathrm{~mol} \mathrm{of} \mathrm{H}_2 \mathrm{O}$ without loss of $\mathrm{CO}_2$. What is the acid?

Ramesh Singh
Ramesh Singh
Numerade Educator
01:21

Problem 49

The following carboxylic acids are unstable and their decomposition products are shown in parentheses: carbonic acid, $(\mathrm{HO})_2 \mathrm{C}=\mathrm{O}\left(\mathrm{CO}_2+\mathrm{H}_2 \mathrm{O}\right)$; carbamic acid, $\mathrm{H}_2 \mathrm{NCOOH}\left(\mathrm{CO}_2+\mathrm{NH}_3\right)$; and chlorocarbonic acid, $\mathrm{ClCOOH}\left(\mathrm{CO}_2+\mathrm{HCl}\right)$. Indicate how the stable compounds below are derived from one or more of these unstable acids. Name those for which a common name is not given.
(a) $\mathrm{Cl}_2 \mathrm{C}=\mathrm{O}$
(b) $\quad\left(\mathrm{H}_2 \mathrm{~N}\right)_2 \mathrm{C}=\mathrm{O}$
(c)
Phosgene
Urea
<smiles>CC(=O)Cl</smiles>
(d) $\left(\mathrm{CH}_3 \mathrm{O}\right)_2 \mathrm{C}=\mathrm{O}$
(e)
<smiles>COC(N)=O</smiles>
(f) $\mathrm{HN}=\mathrm{C}=\mathrm{O}$
Isocyanic acid

Lijeesh Krishnan
Lijeesh Krishnan
Numerade Educator
04:47

Problem 51

Barbiturates are sedative-hypnotic varieties of 5,5-dialkyl substituted barbituric acids. Write the reaction for the formation of Veronal (5,5-diethylbarbituric acid) from the condensation of urea with diethylmalonic ester. [See Problem 17.11(a)].

Tom Rutherford
Tom Rutherford
Numerade Educator
01:57

Problem 52

Indicate the reactions involved and show the structures of the following condensation polymers obtained from the indicated reactants: $(a)$ Nylon 66 from adipic acid and hexamethylene diamine: $(b)$ Nylon 6 from $\varepsilon$ caprolactam; $(c)$ Dacron from methyl terephthalate and ethylene glycol; $(d)$ Glyptal from glycerol and terephthalic acid; (e) polyurethane from diisocyanates and ethylene glyclol.

David Collins
David Collins
Numerade Educator
01:41

Problem 53

Name (a) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{SO}_2 \mathrm{OCH}_3$, (b) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{SO}_2 \mathrm{NH}_2$, (c) $p-\mathrm{BrC}_6 \mathrm{H}_4 \mathrm{CO}_2 \mathrm{Cl}$.
(a) methyl benzenesulfonate, (b) benzenesulfonamide, (c) $p$-bromobenzenesulfonyl chloride (brosyl chloride)

Raghvendra Singh
Raghvendra Singh
Numerade Educator
12:32

Problem 54

Give the product formed when $\mathrm{PhSO}_2 \mathrm{Cl}$ is treated with $(a)$ phenol, $(b)$ aniline, (c) water, $(d)$ excess $\mathrm{Zn}$ and $\mathrm{HCl}$.
(a) phenyl benzenesulfonate, $\mathrm{PhSO}_2 \mathrm{OPh}$; (b) $\mathrm{N}$-phenylbenzenesulfonamide, $\mathrm{PhSO}_2 \mathrm{NHPh}$; $c$ ) benzenesulfonic acid, $\mathrm{PhSO}_2 \mathrm{OH}$, (d) thiophenol, $\mathrm{C}_6 \mathrm{H}_5 \mathrm{SH}$.

Shalini Tyagi
Shalini Tyagi
Numerade Educator
00:48

Problem 57

Prepare methyl 2-methylpropanesulfonate from 1-chloro-2-methylpropane,

Mishal Gul
Mishal Gul
Numerade Educator
05:53

Problem 61

Prepare $\alpha$-methylbutyric acid from ethanol.

Abigail Taye
Abigail Taye
Numerade Educator
01:59

Problem 62

Convert 2-chlorobutanoic acid into 3-chlorobutanoic acid.

Vasu Makani
Vasu Makani
Numerade Educator
05:24

Problem 63

Write structures for the compounds (A) through (D).

Tom Rutherford
Tom Rutherford
Numerade Educator
01:09

Problem 64

Use simple, rapid, test tube reactions to distinguish among hexane, hexanol and hexanoic acid.

Asmita Mehta
Asmita Mehta
Numerade Educator
04:12

Problem 65

Describe the electronic effect of $\mathrm{C}_6 \mathrm{H}_5$ on acidity, if the acid strengths of $\mathrm{C}_6 \mathrm{H}_5 \mathrm{COOH}$ and $\mathrm{HCOOH}$ are $6.3 \times 10^{-5}$ and $1.7 \times 10^{-4}$, respectively.

Anthony Han
Anthony Han
Numerade Educator
07:44

Problem 66

What compounds are formed on heating (a) 1,2,2-cyclohexanetricarboxylic acid, and (b) 1,1,2cyclobutanetricarboxylic acid?

George Bennett
George Bennett
Numerade Educator
03:08

Problem 67

Write structural formulas for the products formed from reaction of $\delta$-valerolactone with: $(a)$ $\mathrm{LiAlH}_4$, then $\mathrm{H}_2 \mathrm{O} ;($ b $) \mathrm{NH}_3 ;(c) \mathrm{CH}_3 \mathrm{OH}$ and $\mathrm{H}_2 \mathrm{SO}_4$ catalyst.

Aadit Sharma
Aadit Sharma
Numerade Educator
03:59

Problem 68

Prepare the mixed anhydride of acetic and propionic acids.

Stefan Kaliszuk
Stefan Kaliszuk
Numerade Educator
04:39

Problem 69

Use ${ }^{14} \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH}$ to synthesize ${ }^{14} \mathrm{CH}_3 \mathrm{CONH}_2$.

Ramesh Singh
Ramesh Singh
Numerade Educator
01:27

Problem 70

Distinguish by chemical tests $($ a $) \mathrm{CH}_3 \mathrm{COCl}$ from $\left(\mathrm{CH}_3 \mathrm{CO}\right)_2 \mathrm{O}$, (b) nitrobenzene from benzamide.

Sydney Atkins
Sydney Atkins
Numerade Educator
02:27

Problem 71

Name the main organic product(s) formed in the following reactions:
(a) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{COOCH}_3+$ excess $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{MgBr}$, then $\mathrm{H}_3 \mathrm{O}^{+}$
(b) $\left(\mathrm{CH}_3\right)_2 \mathrm{CHCH}_2 \mathrm{CH}_2 \mathrm{OH}+\mathrm{C}_6 \mathrm{H}_5 \mathrm{COCl}$
(c) $\mathrm{HCOOCH}_2\left(\mathrm{CH}_2\right)_4 \mathrm{CH}_3+\mathrm{NH}_3$
(d) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{COCl}+\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{COONa}$
(e) $\mathrm{C}_6 \mathrm{H}_5 \mathrm{COBr}+2 \mathrm{C}_6 \mathrm{H}_5 \mathrm{MgBr}$, then $\mathrm{H}_3 \mathrm{O}^{+}$

Catherine Lemar
Catherine Lemar
Numerade Educator

Problem 72

Name and write the structures of the main organic products: $(a) \mathrm{H}_2 \mathrm{C}=\mathrm{CHCH}_2 \mathrm{I}$ heated with $\mathrm{NaCN} ;($ b $) \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CONH}_2$ heated with $\mathrm{P}_4 \mathrm{O}_{10}$; (c) p-iodobenzyl bromide reacted with $\mathrm{CH}_3 \mathrm{COOAg}$; (d) nitration of benzamide.

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07:20

Problem 73

Give steps for the following preparations: (a) 1-phenylpropane from $\beta$-phenylpropionic acid, (b) $\beta$ benzoylpropionic acid from benzene and succinic acid.

Ian Kaigh
Ian Kaigh
Numerade Educator

Problem 74

Identify the substances (A) through (E) in the sequence

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04:28

Problem 75

Give the products from reaction of benzamide, $\mathrm{PhCONH}_2$, with (a) $\mathrm{LiAlH}_4$, then $\mathrm{H}_3 \mathrm{O}^{+}$; (b) $\mathrm{P}_4 \mathrm{H}_{10} ;($ c) hot aqueous $\mathrm{NaOH} ;(d)$ hot aqueous $\mathrm{HCl}$.

Madeline Currie
Madeline Currie
Numerade Educator
03:25

Problem 76

Suggest a synthesis of $\left(\mathrm{CH}_3\right)_3 \mathrm{CCH}=\mathrm{CH}_2$ from $\left(\mathrm{CH}_3\right)_3 \mathrm{CCHOHCH}_3$.

Lottie Adams
Lottie Adams
Numerade Educator
01:41

Problem 77

Assign numbers from 1 for LEAST to 3 for MOST to show the relative ease of acid-catalyzed esterification of:

Kaitlynn Wade
Kaitlynn Wade
Numerade Educator

Problem 78

The ${ }^{18} \mathrm{O}$ of $\mathrm{R}^{18} \mathrm{OH}$ appears in the ester, not in the water, when the alcohol reacts with a carboxylic acid. Offer a mechanism consistent with this finding.

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02:24

Problem 79

Show how phosgene,
<smiles>O=C(Cl)Cl</smiles>
is used to prepare (a) urea, (b) methyl carbonate, (c) ethyl chlorocarbonate, (d) ethyl N-ethylcarbamate (a urethane), (e) ethyl isocyanate $\left(\mathrm{C}_2 \mathrm{H}_5-\mathrm{N}=\mathrm{C}=\mathrm{O}\right)$.

Sima Sarker
Sima Sarker
Numerade Educator
08:31

Problem 80

What carboxylic acid (A) has a neutralization equivalent (NE) of 52 and decomposes on heating to yield $\mathrm{CO}_2$ and a carboxylic acid (B) with an NE of 60 ?

Zubair Abdulla
Zubair Abdulla
Numerade Educator

Problem 81

An acyclic compound, $\mathrm{C}_6 \mathrm{H}_{12} \mathrm{O}_2$, has strong ir bands at 1740,1250 , and $1060 \mathrm{~cm}^{-1}$, and no bands at frequencies greater than $2950 \mathrm{~cm}^{-1}$. The nmr spectrum has two singlets at $\delta=3.4(1 \mathrm{H})$ and $\delta=1.0(3 \mathrm{H})$. What is the compound?

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02:19

Problem 82

Predict the base (most prominent) peak in the mass spectrum of the compound in Problem 16.81 .

Madeline Currie
Madeline Currie
Numerade Educator
04:48

Problem 83

Identify the compound $\mathrm{C}_4 \mathrm{H}_{11} \mathrm{O}_2 \mathrm{SCl}(\mathrm{A})$, and also compounds (B), (C), and (D), in the reactions:

Ian Kaigh
Ian Kaigh
Numerade Educator
07:18

Problem 84

(a) (S)-sec- $\mathrm{C}_4 \mathrm{H}_9 \mathrm{OH}$, which has an optical rotation of $+13.8^{\circ}$, is reacted with tosyl chloride (see Problem 16.55) and the product is saponified. (b) Another sample of this alcohol is treated with benzoyl chloride and the product is also hydrolyzed with base. What is the rotation of the $\sec -\mathrm{C}_4 \mathrm{H}_9 \mathrm{OH}$ from each reaction?

Nicholas Sacco
Nicholas Sacco
Numerade Educator
02:39

Problem 85

Write structural formulas for the organic compounds (I) through (XI) and show the stereochemistry of (X) and (XI). (Write Ts for the tosyl group.)

Lottie Adams
Lottie Adams
Numerade Educator
04:15

Problem 86

Why are sulfonic acid derivatives less reactive toward nucleophilic substitutions than are the corresponding acyl derivatives?

Ian Kaigh
Ian Kaigh
Numerade Educator
01:03

Problem 87

(a) Show the mers of the following condensation polymers, formed from the two indicated monomers: (i) Polycarbonate (Lexan), phosgene, $\mathrm{Cl}_2 \mathrm{C}=\mathrm{O}+\left(\mathrm{HOC}_6 \mathrm{H}_4\right)_2 \mathrm{C}\left(\mathrm{CH}_3\right)_2$ (tough and optically clear); (ii) Kodel,

David Collins
David Collins
Numerade Educator
03:00

Problem 88

Which would have the higher $\lambda_{\max }$ value in the uv, benzoic acid or cinnamic acid, $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}=\mathrm{CHCOOH}$ ? Why?

Kim Trang Nguyen
Kim Trang Nguyen
Numerade Educator
11:04

Problem 89

Tell how propanal and propanoic acid can be distinguished by their $(a)$ ir, $(b) \mathrm{nmr},(c) \mathrm{cmr}$ spectra.

Temi Ajayi
Temi Ajayi
Numerade Educator