Reduction occurs via a typical nucleophilic acyl substitution mechanism in which a hydride ion ( $\mathrm{H}:^{-}$) adds to the carbonyl group, yielding a tetrahedral intermediate that expels $\mathrm{Cl}^{-}$. The net effect is a substitution of -Cl by -H to yield an aldehyde, which is then further reduced by $\mathrm{LiAlH}_{4}$ in a second step to yield the primary alcohol.
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Benzoyl chloride
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0750.jpg?height=92&width=219&top_left_y=434&top_left_x=934)
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Conversion of Acid Chlorides into Alcohols: Reduction and Grignard Reaction -

Benzyl alcohol (96\%)


Grignard reagents react with acid chlorides to yield tertiary alcohols with two identical substituents. The mechanism of the reaction is similar to that of $\mathrm{LiAlH}_{4}$ reduction. The first equivalent of Grignard reagent adds to the acid chloride, loss of $\mathrm{Cl}^{-}$from the tetrahedral intermediate yields a ketone, and a second equivalent of Grignard reagent immediately adds to the ketone to produce an alcohol.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0750.jpg?height=310&width=1212&top_left_y=799&top_left_x=454)


Conversion of Acid Chlorides into Ketones: Diorganocopper Reaction
The ketone intermediate formed in the reaction of an acid chloride with a Grignard reagent can't usually be isolated because addition of the second equivalent of organomagnesium reagent occurs too rapidly. A ketone can, however, be isolated from the reaction of an acid chloride with a lithium diorganocopper (Gilman) reagent, $\mathrm{Li}^{+} \mathrm{R}_{2} \mathrm{Cu}^{-}$. The reaction occurs by initial nucleophilic acyl substitution on the acid chloride by the diorganocopper anion to yield an acyl diorganocopper intermediate, followed by loss of $\mathrm{R}^{\prime} \mathrm{Cu}$ and formation of the ketone.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0750.jpg?height=215&width=985&top_left_y=1454&top_left_x=570)


An acid An acyl A ketone chloride <br> diorganocopper -

The reaction is generally carried out at $-78^{\circ} \mathrm{C}$ in ether solution, and yields are often excellent. For example, manicone, a substance secreted by male ants to coordinate ant pairing and mating, has been synthesized by reaction of lithium diethylcopper with (E)-2,4-dimethyl-2-hexenoyl chloride.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0750.jpg?height=285&width=1050&top_left_y=1901&top_left_x=535)


Note that the diorganocopper reaction occurs only with acid chlorides. Carboxylic acids, esters, acid anhydrides, and amides do not react with lithium diorganocopper reagents.


PROBLEM How could you prepare the following ketones by reaction of an acid chloride with a lithium 21-13 diorganocopper reagent?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0751.jpg?height=402&width=1218&top_left_y=176&top_left_x=405)


An acid An acyl A ketone chloride <br> diorganocopper - 21.5 Chemistry of Acid Anhydrides


Preparation of Acid Anhydrides -

Acid anhydrides are typically prepared by nucleophilic acyl substitution reaction of an acid chloride with a carboxylate anion, as we saw in the previous section. Both symmetrical and unsymmetrical acid anhydrides can be prepared in this way.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0751.jpg?height=272&width=1058&top_left_y=875&top_left_x=536)


Reactions of Acid Anhydrides -

The chemistry of acid anhydrides is similar to that of acid chlorides, although anhydrides react more slowly. Thus, acid anhydrides react with water to form acids, with alcohols to form esters, with amines to form amides, and with $\mathrm{LiAlH}_{4}$ to form primary alcohols. Only the ester- and amide-forming reactions are commonly used, however.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0751.jpg?height=134&width=565&top_left_y=1429&top_left_x=650)


Reactions of Acid Anhydrides -

Alcoholysis
Aminolysis
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0751.jpg?height=376&width=1098&top_left_y=1617&top_left_x=511)


Conversion of Acid Anhydrides into Esters -

Acetic anhydride is often used to prepare acetate esters from alcohols. For example, aspirin (acetylsalicylic acid) is prepared commercially by the acetylation of $o$-hydroxybenzoic acid (salicylic acid) with acetic anhydride.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0751.jpg?height=308&width=1134&top_left_y=2139&top_left_x=506)


Aspirin (an ester)


Conversion of Acid Anhydrides into Amides -

Acetic anhydride is also commonly used to prepare $N$-substituted acetamides from amines. For example, acetaminophen, a drug used in over-the-counter analgesics such as Tylenol, is prepared by reaction of $p$-hydroxyaniline with acetic anhydride. Only the more nucleophilic $-\mathrm{NH}_{2}$ group reacts rather than the less nucleophilic - OH group.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0752.jpg?height=314&width=1254&top_left_y=434&top_left_x=433)


Notice in both of the previous reactions that only "half" of the anhydride molecule is used, while the other half acts as the leaving group during the nucleophilic acyl substitution step and produces acetate ion as a by-product. Thus, anhydrides are inefficient, and acid chlorides are normally preferred for introducing acyl substituents other than acetyl groups.


PROBLEM Write the mechanism of the reaction between $p$-hydroxyaniline and acetic anhydride to prepare
21-14 acetaminophen.
PROBLEM What product would you expect from reaction of one equivalent of methanol with a cyclic
21-15 anhydride, such as phthalic anhydride (1,2-benzenedicarboxylic anhydride)? What is the fate of the second "half" of the anhydride?
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Phthalic anhydride -


Phthalic anhydride - 21.6 Chemistry of Esters

Esters are among the most widespread of all naturally occurring compounds. Many simple esters are pleasantsmelling liquids that are responsible for the fragrant odors of fruits and flowers. For example, methyl butanoate is found in pineapple oil, and isopentyl acetate is a constituent of banana oil. The ester linkage is also present in animal fats and in many biologically important molecules.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0752.jpg?height=296&width=782&top_left_y=1722&top_left_x=628)
$A$ fat
$\left(R=C_{11-17}\right.$ chains $)$


The chemical industry uses esters for a variety of purposes. Ethyl acetate, for instance, is a commonly used solvent, and dialkyl phthalates are used as plasticizers to keep polymers from becoming brittle. You may be aware that there is current concern about the possible toxicity of phthalates at high concentrations, although a recent assessment by the U.S. Food and Drug Administration found the risk to be minimal for most people, with the possible exception of male infants.
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Dibutyl phthalate (a plasticizer)


Preparation of Esters -

Esters are usually prepared from carboxylic acids by the methods already discussed. Thus, carboxylic acids are converted directly into esters by $S_{N} 2$ reaction of a carboxylate ion with a primary alkyl halide or by Fischer esterification of a carboxylic acid with an alcohol in the presence of a mineral acid catalyst. In addition, acid chlorides are converted into esters by treatment with an alcohol in the presence of base (Section 21.4).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0753.jpg?height=513&width=925&top_left_y=719&top_left_x=600)


Reactions of Esters -

Esters undergo the same kinds of reactions that we've seen for other carboxylic acid derivatives, but they are less reactive toward nucleophiles than either acid chlorides or anhydrides. All their reactions are applicable to both acyclic and cyclic esters, called lactones.
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A lactone (cyclic ester) -

Conversion of Esters into Carboxylic Acids: Hydrolysis
An ester is hydrolyzed, either by aqueous base or aqueous acid, to yield a carboxylic acid plus an alcohol.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0753.jpg?height=190&width=721&top_left_y=1713&top_left_x=702)


A lactone (cyclic ester) -

Ester hydrolysis in basic solution is called saponification, after the Latin word sapo, meaning "soap." We'll see in Section 27.2 that soap is in fact made by boiling animal fat with aqueous base to hydrolyze the ester linkages.


A lactone (cyclic ester) -

As shown in FIGURE 21.8, ester hydrolysis occurs through a typical nucleophilic acyl substitution pathway in which hydroxide ion is the nucleophile that adds to the ester carbonyl group to give a tetrahedral intermediate. Loss of alkoxide ion then gives a carboxylic acid, which is deprotonated to give the carboxylate ion. Addition of aqueous HCl , in a separate step after the saponification is complete, protonates the carboxylate ion and gives the carboxylic acid.


FIGURE 21.8 MECHANISM -

Mechanism of base-induced ester hydrolysis (saponification).
Nucleophilic addition of hydroxide ion
to the ester carbonyl group gives the
usual tetrahedral alkoxide
intermediate.
2 Elimination of alkoxide ion then
generates the carboxylic acid.
3 Alkoxide ion abstracts the acidic
proton from the carboxylic acid and
yields a carboxylate ion.
4 Protonation of the carboxylate ion
by addition of aqueous mineral acid
in a separate step then gives the
free carboxylic acid.


FIGURE 21.8 MECHANISM -

The mechanism shown in FIGURE 21.8 is supported by isotope-labeling studies. When ethyl propanoate labeled with ${ }^{18} \mathrm{O}$ in the ether-like oxygen is hydrolyzed in aqueous NaOH , the ${ }^{18} \mathrm{O}$ label shows up exclusively in the ethanol product. None of the label remains with the propanoic acid, indicating that saponification occurs by cleavage of the $\mathrm{C}-\mathrm{OR}^{\prime}$ bond rather than the $\mathrm{CO}-\mathrm{R}^{\prime}$ bond.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0754.jpg?height=161&width=1015&top_left_y=1860&top_left_x=552)


FIGURE 21.8 MECHANISM -

Acid-catalyzed ester hydrolysis can occur by more than one mechanism, depending on the structure of the ester. The usual pathway, however, is just the reverse of a Fischer esterification reaction (Section 21.3). As shown in FIGURE 21.9, the ester is first activated toward nucleophilic attack by protonation of the carboxyl oxygen atom, and nucleophilic addition of water then occurs. Transfer of a proton and elimination of alcohol yields the carboxylic acid. Because this hydrolysis reaction is the reverse of a Fischer esterification reaction, FIGURE 21.9 is the reverse of FIGURE 21.5.


FIGURE 21.9 MECHANISM -

Mechanism of acid-catalyzed ester hydrolysis. The forward reaction is a hydrolysis; the back-reaction is a Fischer esterification and is thus the reverse of FIGURE 21.5.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0755.jpg?height=1465&width=1189&top_left_y=433&top_left_x=468)


FIGURE 21.9 MECHANISM -

Ester hydrolysis is common in biological chemistry, particularly in the digestion of dietary fats and oils. We'll save a complete discussion of the mechanistic details of fat hydrolysis until Section 29.2 but will note for now that the reaction is catalyzed by various lipase enzymes and involves two sequential nucleophilic acyl substitution reactions. The first is a transesterification reaction in which an alcohol group on the lipase adds to an ester linkage in the fat molecule to give a tetrahedral intermediate that expels alcohol and forms an acyl enzyme intermediate. The second is an addition of water to the acyl enzyme, followed by expulsion of the enzyme to give a hydrolyzed acid and a regenerated enzyme.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0756.jpg?height=665&width=1201&top_left_y=177&top_left_x=454)


FIGURE 21.9 MECHANISM -

PROBLEM Why is the saponification of an ester irreversible? In other words, why doesn't treatment of a
21-16 carboxylic acid with an alkoxide ion yield an ester?


Conversion of Esters into Amides: Aminolysis -

Esters react with ammonia and amines to yield amides. The reaction is not often used, however, because it's usually easier to prepare an amide by starting with an acid chloride (Section 21.4).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0756.jpg?height=272&width=969&top_left_y=1122&top_left_x=578)


Conversion of Esters into Alcohols: Reduction -

Esters are easily reduced by treatment with $\mathrm{LiAlH}_{4}$ to yield primary alcohols (Section 17.4).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0756.jpg?height=180&width=1213&top_left_y=1512&top_left_x=453)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0756.jpg?height=231&width=741&top_left_y=1695&top_left_x=665)


A lactone -

The mechanism of ester reduction is similar to that of acid chloride reduction in that a hydride ion first adds to the carbonyl group, followed by elimination of alkoxide ion to yield an aldehyde. Further reduction of the aldehyde gives the primary alcohol.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0756.jpg?height=268&width=1398&top_left_y=2135&top_left_x=361)


A lactone -

The aldehyde intermediate can be isolated if 1 equivalent of diisobutylaluminum hydride (DIBAH, or DIBALH ) is used as the reducing agent instead of $\mathrm{LiAlH}_{4}$. The reaction has to be carried out at $-78{ }^{\circ} \mathrm{C}$ to avoid further reduction to the alcohol. Such partial reductions of carboxylic acid derivatives to aldehydes also occur
in numerous biological pathways, although the substrate is either a thioester or acyl phosphate rather than an ester.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0757.jpg?height=331&width=1291&top_left_y=298&top_left_x=417)


A lactone -

PROBLEM What product would you expect from the reaction of butyrolactone with $\mathrm{LiAlH}_{4}$ ? With DIBAH?
21-17
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0757.jpg?height=172&width=367&top_left_y=700&top_left_x=410)


A lactone -

PROBLEM Show the products you would obtain by reduction of the following esters with $\mathrm{LiAlH}_{4}$ :


A lactone -


A lactone -

Conversion of Esters into Alcohols: Grignard Reaction
Esters react with 2 equivalents of a Grignard reagent to yield a tertiary alcohol in which two of the substituents are identical (Section 17.5). The reaction occurs by the usual nucleophilic substitution mechanism to give an intermediate ketone, which reacts further with the Grignard reagent to yield a tertiary alcohol.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0757.jpg?height=315&width=960&top_left_y=1401&top_left_x=580)


A lactone -

PROBLEM What ester and what Grignard reagent might you start with to prepare the following alcohols?


A lactone - 21.7 Chemistry of Amides

Amides, like esters, are abundant in all living organisms. Proteins, nucleic acids, and many pharmaceutical agents have amide functional groups. The reason for this abundance of amides is that they are stable in the aqueous conditions found in living organisms. Amides are the least reactive of the common acid derivatives and undergo relatively few nucleophilic acyl substitution reactions.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0758.jpg?height=197&width=500&top_left_y=346&top_left_x=281)


A lactone - 21.7 Chemistry of Amides


A lactone - 21.7 Chemistry of Amides

Uridine 5 '-phosphate (a ribonucleotide)


Preparation of Amides -

Amides are usually prepared by reaction of an amine with an acid chloride (Section 21.4). Ammonia, monosubstituted amines, and disubstituted amines all undergo the reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0758.jpg?height=381&width=736&top_left_y=826&top_left_x=689)


Reactions of Amides -


Conversion of Amides into Carboxylic Acids: Hydrolysis -

Amides undergo hydrolysis to yield carboxylic acids plus ammonia or an amine upon heating in either aqueous acid or aqueous base. The conditions required for amide hydrolysis are more extreme than those required for the hydrolysis of acid chlorides or esters, but the mechanisms are similar. Acidic hydrolysis reaction occurs by nucleophilic addition of water to the protonated amide, followed by transfer of a proton from oxygen to nitrogen to make the nitrogen a better leaving group, and subsequent elimination. The steps are reversible, with the equilibrium shifted toward product by protonation of $\mathrm{NH}_{3}$ in the final step.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0758.jpg?height=570&width=1395&top_left_y=1623&top_left_x=365)

Basic hydrolysis occurs by nucleophilic addition of $\mathrm{OH}^{-}$to the amide carbonyl group, followed by elimination of amide ion $\left({ }^{-} \mathrm{NH}_{2}\right)$ and subsequent deprotonation of the initially formed carboxylic acid by ammonia. The steps are reversible, with the equilibrium shifted toward product by the final deprotonation of the carboxylic acid. Basic hydrolysis is substantially more difficult than the analogous acid-catalyzed reaction because amide ion is a very poor leaving group, making the elimination step difficult.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0759.jpg?height=247&width=1445&top_left_y=191&top_left_x=340)


Amide hydrolysis is common in biological chemistry. Just as the hydrolysis of esters is the initial step in the digestion of dietary fats, the hydrolysis of amides is the initial step in the digestion of dietary proteins. The reaction is catalyzed by protease enzymes and occurs by a mechanism almost identical to what we just saw for fat hydrolysis. That is, an initial nucleophilic acyl substitution of an alcohol group in the enzyme on an amide linkage in the protein gives an acyl enzyme intermediate, which then undergoes hydrolysis.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0759.jpg?height=657&width=1240&top_left_y=669&top_left_x=437)


Conversion of Amides into Amines: Reduction
Like other carboxylic acid derivatives, amides can be reduced by $\mathrm{LiAlH}_{4}$. The product of the reduction, however, is an amine rather than an alcohol. The net effect of an amide reduction is thus the conversion of the amide carbonyl group into a methylene group $\left(\mathrm{C}=\mathrm{O} \longrightarrow \mathrm{CH}_{2}\right)$. This kind of reaction is specific to amides and does not occur with other carboxylic acid derivatives.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0759.jpg?height=188&width=1050&top_left_y=1584&top_left_x=532)
$\boldsymbol{N}$-Methyldodecanamide
Dodecylmethylamine (95\%)
Amide reduction occurs by nucleophilic addition of hydride ion to the amide carbonyl group, followed by expulsion of the oxygen atom as an aluminate anion leaving group to give an iminium ion intermediate. The intermediate iminium ion is further reduced by $\mathrm{LiAlH}_{4}$ to yield the amine.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0759.jpg?height=264&width=1319&top_left_y=1977&top_left_x=403)


The reaction is effective with both acyclic and cyclic amides, or lactams, and is a good method for preparing cyclic amines.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0760.jpg?height=226&width=795&top_left_y=185&top_left_x=654)


WORKED EXAMPLE 21.4 -


Synthesizing an Amine from an Amide -


Strategy -

Reduction of an amide with $\mathrm{LiAlH}_{4}$ yields an amine. To find the starting material for synthesis of N -ethylaniline, look for a $\mathrm{CH}_{2}$ position next to the nitrogen atom and replace that $\mathrm{CH}_{2}$ by $\mathrm{C}=\mathrm{O}$. In this case, the amide is $N$-phenylacetamide.


Strategy -

Solution
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0760.jpg?height=278&width=1041&top_left_y=1113&top_left_x=542)


Strategy -

PROBLEM How would you convert $N$-ethylbenzamide to each of the following products?
21-20 (a) Benzoic acid
(b) Benzyl alcohol
(c) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NHCH}_{2} \mathrm{CH}_{3}$


Strategy -

PROBLEM How would you use the reaction of an amide with $\mathrm{LiAlH}_{4}$ as the key step in going from
21-21 bromocyclohexane to ( $N, N$-dimethylaminomethyl)cyclohexane? Write all the steps in the reaction sequence.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0760.jpg?height=145&width=625&top_left_y=1689&top_left_x=414)
(N,N-Dimethylaminomethyl)cyclohexane


Strategy - 21.8 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives

As mentioned in the chapter introduction, the substrate for a nucleophilic acyl substitution reaction in living organisms is generally either a thioester ( $\mathrm{RCOSR}{ }^{\prime}$ ) or an acyl phosphate ( $\mathrm{RCO}_{2} \mathrm{PO}_{3}{ }^{2-}$ or $\mathrm{RCO}_{2} \mathrm{PO}_{3} \mathrm{R}^{\prime-}$ ). Neither is as reactive as an acid chloride or acid anhydride, yet both are stable enough to exist in living organisms while still reactive enough to undergo acyl substitution.


Acyl CoA's, such as acetyl CoA, are the most common thioesters in nature. Coenzyme A, abbreviated CoA, is a thiol formed by a phosphoric anhydride linkage ( $\mathrm{O}=\mathrm{P}-\mathrm{O}-\mathrm{P}=\mathrm{O}$ ) between phosphopantetheine and adenosine $3^{\prime}, 5^{\prime}$-bisphosphate. (The prefix bis- means "two" and indicates that adenosine $3^{\prime}, 5^{\prime}$-bisphosphate has two phosphate groups, one on C3' and one on $\mathrm{C}^{\prime}$.) Reaction of coenzyme A with an acyl phosphate or acyl adenylate gives acyl CoA (FIGURE 21.10). As we saw in Section 21.3 (FIGURE 21.7), formation of the acyl adenylate occurs by reaction of a carboxylic acid with ATP and is itself a nucleophilic acyl substitution reaction that takes place on phosphorus.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0761.jpg?height=394&width=993&top_left_y=193&top_left_x=571)
Adenosine $\mathbf{3}^{\prime}$, $\mathbf{5}^{\prime}$-bisphosphate


Coenzyme A (CoA) -


Acetyl CoA -

FIGURE 21.10 Formation of the thioester acetyl CoA by nucleophilic acyl substitution reaction of coenzyme $A$ (CoA) with acetyl adenylate.


Acetyl CoA -

Once formed, an acyl CoA is a substrate for further nucleophilic acyl substitution reactions. For example, N -acetylglucosamine, a component of cartilage and other connective tissues, is synthesized by an aminolysis reaction between glucosamine and acetyl CoA.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0761.jpg?height=348&width=1229&top_left_y=1620&top_left_x=445)


Acetyl CoA -

Another example of a nucleophilic acyl substitution reaction on a thioester-this one a substitution by hydride ion to effect the partial reduction of a thioester to an aldehyde-occurs in the biosynthesis of mevaldehyde, an intermediate in terpenoid synthesis, which we'll discuss in some detail in Section 27.5. In this reaction, (3S)-3-hydroxy-3-methylglutaryl CoA is reduced by hydride donation from NADPH.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0762.jpg?height=502&width=1557&top_left_y=188&top_left_x=281)


Acetyl CoA -

PROBLEM Write the mechanism of the reaction shown in Figure 21.10 between coenzyme A and acetyl
21-22 adenylate to give acetyl CoA.


Acetyl CoA - 21.9 Polyamides and Polyesters: Step-Growth Polymers

When an amine reacts with an acid chloride, an amide is formed. What would happen, though, if a diamine and a diacid chloride were allowed to react? Each partner would form two amide bonds, linking more and more molecules together until a giant polyamide resulted. In the same way, reaction of a diol with a diacid would lead to a polyester.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0762.jpg?height=112&width=1069&top_left_y=1055&top_left_x=512)


A diamine A diacid chloride


A polyamide (nylon)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0762.jpg?height=109&width=1171&top_left_y=1252&top_left_x=477)