Reactivity -

Electronically, we find that strongly polarized acyl compounds react more readily than less polar ones. Thus, acid chlorides are the most reactive because the electronegative chlorine atom withdraws electrons from the carbonyl carbon, whereas amides are the least reactive. Although subtle, electrostatic potential maps of various carboxylic acid derivatives indicate these differences by the relative blueness on the $\mathrm{C}=\mathrm{O}$ carbons. Acyl phosphates are hard to place on this scale because they are not often used in the laboratory, but in biological systems they appear to be somewhat more reactive than thioesters.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0737.jpg?height=239&width=277&top_left_y=214&top_left_x=260)
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Amide
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0737.jpg?height=245&width=329&top_left_y=208&top_left_x=556)
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Ester
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Thioester
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Acid anhydride
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src="data:image/svg+xml;base64,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Reactivity -

Acid chloride


Reactivity -

The way in which various substituents affect the polarization of a carbonyl group is similar to the way they affect the reactivity of an aromatic ring toward electrophilic substitution (Section 16.4). A chlorine substituent, for example, inductively withdraws electrons from an acyl group in the same way that it withdraws electrons from and thus deactivates an aromatic ring. Similarly, amino, methoxyl, and methylthio substituents donate electrons to acyl groups by resonance in the same way that they donate electrons to, and thus activate, aromatic rings.


Reactivity -

As a consequence of these reactivity differences, it's usually possible to convert a more reactive acid derivative into a less reactive one. Acid chlorides, for instance, can be directly converted into anhydrides, thioesters, esters, and amides, but amides can't be directly converted into esters, thioesters, anhydrides, or acid chlorides. Remembering the reactivity order is therefore a way to keep track of a large number of reactions (FIGURE 21.3). Another consequence, as noted previously, is that only acyl phosphates, thioesters, esters, and amides are commonly found in nature. Acid halides and acid anhydrides react so rapidly with water that they can't exist for long in living organisms.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0737.jpg?height=855&width=1096&top_left_y=1421&top_left_x=512)


Reactivity -

FIGURE 21.3 Interconversions of carboxylic acid derivatives. A more reactive acid derivative can be converted into a less reactive one, but not vice versa.


Reactivity -

In studying the chemistry of carboxylic acid derivatives in the next few sections, we'll be concerned largely with the reactions of just a few nucleophiles and will see that the same kinds of reactions tend to reoccur (FIGURE 21.4).


Reactivity -

- Hydrolysis
- Alcoholysis
- Aminolysis
- Reduction
- Grignard reaction


Reactivity -

Reaction with water to yield a carboxylic acid
Reaction with an alcohol to yield an ester
Reaction with ammonia or an amine to yield an amide
Reaction with a hydride reducing agent to yield an aldehyde or an alcohol
Reaction with an organometallic reagent to yield a ketone or an alcohol
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0738.jpg?height=562&width=1099&top_left_y=467&top_left_x=513)


Reactivity -

FIGURE 21.4 Some general reactions of carboxylic acid derivatives.


WORKED EXAMPLE 21.1 -


Predicting the Product of a Nucleophilic Acyl Substitution Reaction -

Predict the product of the following nucleophilic acyl substitution reaction of benzoyl chloride with 2-propanol:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0738.jpg?height=207&width=492&top_left_y=1298&top_left_x=811)


Benzoyl chloride


Strategy -

A nucleophilic acyl substitution reaction involves the substitution of a nucleophile for a leaving group in a carboxylic acid derivative. Identify the leaving group ( $\mathrm{Cl}^{-}$in the case of an acid chloride) and the nucleophile (an alcohol in this case), and replace one by the other. The product is isopropyl benzoate.


Strategy -

Solution
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0738.jpg?height=326&width=789&top_left_y=1843&top_left_x=668)


Strategy -


Strategy -

PROBLEM Predict the products of the following nucleophilic acyl substitution reactions:
21-5
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0739.jpg?height=315&width=1142&top_left_y=187&top_left_x=410)


Strategy -

PROBLEM The following structure represents a tetrahedral alkoxide ion intermediate formed by addition of a 21-6 nucleophile to a carboxylic acid derivative. Identify the nucleophile, the leaving group, the starting acid derivative, and the ultimate product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0739.jpg?height=354&width=500&top_left_y=685&top_left_x=430)


Strategy - 21.3 Reactions of Carboxylic Acids

The direct nucleophilic acyl substitution of a carboxylic acid is difficult because -OH is a poor leaving group (Section 11.3). Thus, it's usually necessary to enhance the reactivity of the acid, either by using a strong acid catalyst to protonate the carboxyl and make it a better acceptor or by converting the - OH into a better leaving group. Under the right circumstances, however, acid chlorides, anhydrides, esters, and amides can all be prepared from carboxylic acids by nucleophilic acyl substitution reactions.


Conversion of Carboxylic Acids into Acid Chlorides -


2,4,6-Trimethylbenzoic acid
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0739.jpg?height=297&width=600&top_left_y=1494&top_left_x=1004)


2,4,6-Trimethylbenzoyl -

chloride (90\%)This reaction occurs by a nucleophilic acyl substitution pathway in which the carboxylic acid is first converted into an acyl chlorosulfite intermediate, thereby replacing the -OH of the acid with a much better leaving group. The chlorosulfite then reacts with a nucleophilic chloride ion. You might recall from Section 17.6 that an analogous chlorosulfite is involved in the reaction of an alcohol with $\mathrm{SOCl}_{2}$ to yield an alkyl chloride.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0739.jpg?height=201&width=1367&top_left_y=2076&top_left_x=379)


2,4,6-Trimethylbenzoyl -

Carboxylic acid


2,4,6-Trimethylbenzoyl -

A chlorosulfite
Acid chloride


Conversion of Carboxylic Acids into Acid Anhydrides -

Acid anhydrides can be derived from two molecules of carboxylic acid by heating to remove 1 equivalent of water. Because of the high temperatures needed, however, only acetic anhydride is commonly prepared this
way.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0740.jpg?height=190&width=825&top_left_y=260&top_left_x=650)


Conversion of Carboxylic Acids into Esters -

Perhaps the most useful reaction of carboxylic acids is their conversion into esters. There are many methods for accomplishing this, including the $\mathrm{S}_{\mathrm{N}} 2$ reaction of a carboxylate anion with a primary alkyl halide that we saw in Section 11.3.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0740.jpg?height=134&width=1199&top_left_y=692&top_left_x=463)


Sodium butanoate -

Methyl butanoate (97\%)
Esters can also be synthesized by an acid-catalyzed nucleophilic acyl substitution reaction of a carboxylic acid with an alcohol, a process called the Fischer esterification reaction. Unfortunately, the need for an excess of a liquid alcohol as solvent effectively limits the method to the synthesis of methyl, ethyl, propyl, and butyl esters.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0740.jpg?height=264&width=1158&top_left_y=1039&top_left_x=478)


Sodium butanoate -

The mechanism of the Fischer esterification reaction is shown in FIGURE 21.5. Carboxylic acids are not reactive enough to undergo nucleophilic addition directly, but their reactivity is greatly enhanced in the presence of a strong acid such as HCl or $\mathrm{H}_{2} \mathrm{SO}_{4}$. The mineral acid protonates the carbonyl-group oxygen atom, thereby giving the carboxylic acid a positive charge and rendering it much more reactive toward nucleophiles. Subsequent loss of water from the tetrahedral intermediate yields the ester product.


FIGURE 21.5 MECHANISM -

Mechanism of Fischer esterification. The reaction is an acid-catalyzed, nucleophilic acyl substitution of a carboxylic acid.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0741.jpg?height=1516&width=1083&top_left_y=386&top_left_x=521)


FIGURE 21.5 MECHANISM -

The net effect of Fischer esterification is substitution of an -OH group by -OR'. All steps are reversible, and the reaction typically has an equilibrium constant close to 1 . Thus, the reaction can be driven in either direction by the choice of reaction conditions. Ester formation is favored when a large excess of alcohol is used as solvent, but carboxylic acid formation is favored when a large excess of water is present.


FIGURE 21.5 MECHANISM -

Evidence in support of the mechanism shown in FIGURE 21.5 comes from isotope-labeling experiments. When ${ }^{18} \mathrm{O}$-labeled methanol reacts with benzoic acid, the methyl benzoate produced is found to be ${ }^{18} \mathrm{O}$-labeled whereas the water produced is unlabeled. Thus, it is the $\mathrm{C}-\mathrm{OH}$ bond of the carboxylic acid that is broken during the reaction rather than the $\mathrm{CO}-\mathrm{H}$ bond and the $\mathrm{RO}-\mathrm{H}$ bond of the alcohol that is broken rather than the $\mathrm{R}-\mathrm{OH}$ bond.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0742.jpg?height=232&width=1082&top_left_y=193&top_left_x=516)


WORKED EXAMPLE 21.2 -


Synthesizing an Ester from an Acid -


Strategy -

Begin by identifying the two parts of the ester. The acyl part comes from the carboxylic acid and the -OR part comes from the alcohol. In this case, the target molecule is propyl o-bromobenzoate, so it can be prepared by treating $o$-bromobenzoic acid with 1-propanol.


Solution -


Solution -

PROBLEM How might you prepare the following esters from the corresponding acids?


Solution -

PROBLEM If the following molecule is treated with acid catalyst, an intramolecular esterification reaction
21-8 occurs. What is the structure of the product? (Intramolecular means within the same molecule.)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0742.jpg?height=258&width=549&top_left_y=1817&top_left_x=425)


Conversion of Carboxylic Acids into Amides -

Amides are difficult to prepare by direct reaction of carboxylic acids with amines because amines are bases that convert acidic carboxyl groups into their unreactive carboxylate anions. Thus, the - OH must be replaced by a better, nonacidic leaving group to carry out a nucleophilic acyl substitution. In practice, amides are often prepared by activating the carboxylic acid with a carbodiimide ( $\mathrm{R}-\mathrm{N}=\mathrm{C}=\mathrm{N}-\mathrm{R}$ ), followed by addition of the amine. Dicyclohexylcarbodiimide (DCC) and 1-ethyl-3-(3-dimethylaminopropylcarbodiimide (EDEC) are commonly used.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0743.jpg?height=243&width=982&top_left_y=193&top_left_x=512)


Dicyclohexylcarbodiimide 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide


As shown in FIGURE 21.6, the acid first adds to a $\mathrm{C}=\mathrm{N}$ double bond of DCC , and nucleophilic acyl substitution by amine then ensues. Alternatively, and depending on the reaction solvent, the reactive acyl intermediate might also react with a second equivalent of carboxylate ion to generate an acid anhydride that then reacts with the amine. The product from either pathway is the same.


FIGURE 21.6 MECHANISM -

Mechanism of amide formation by reaction of a carboxylic acid and an amine with dicyclohexylcarbodiimide (DCC).


FIGURE 21.6 MECHANISM -

Dicyclohexylcarbodiimide is first protonated by the carboxylic acid to make it a better acceptor.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0744.jpg?height=1406&width=607&top_left_y=414&top_left_x=927)
(2) The carboxylate then adds to the protonated carbodiimide to yield a reactive acylating agent.
(3) Nucleophilic attack of the amine on the acylating agent gives a tetrahedral intermediate. dicyclohexylurea and gives the amide.
(4) $\downarrow$
<img class="imgSvg" id = "m6sn3p0wpjh2dtxs5mn" 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![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0744.jpg?height=120&width=204&top_left_y=1962&top_left_x=974)


FIGURE 21.6 MECHANISM -


FIGURE 21.6 MECHANISM -

Dicyclohexylurea


FIGURE 21.6 MECHANISM -

We'll see in Section 26.7 that this carbodiimide method of amide formation is the key step in the laboratory synthesis of small proteins, or peptides. For instance, when one amino acid with its $\mathrm{NH}_{2}$ rendered unreactive and a second amino acid with its $-\mathrm{CO}_{2} \mathrm{H}$ rendered unreactive are treated with carbodiimide, a dipeptide is formed.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0745.jpg?height=188&width=1112&top_left_y=188&top_left_x=504)


FIGURE 21.6 MECHANISM -

Amino acid 1
Amino acid 2
A dipeptide


Conversion of Carboxylic Acids into Alcohols -

We said in Section 17.4 that carboxylic acids are reduced by $\mathrm{LiAlH}_{4}$ to give primary alcohols, but we deferred a discussion of the reaction mechanism at that time. In fact, the reduction is a nucleophilic acyl substitution reaction in which -H replaces -OH to give an aldehyde that is further reduced by nucleophilic addition to produce a primary alcohol. The aldehyde intermediate is much more reactive than the starting acid, so it reacts instantly and is not isolated.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0745.jpg?height=240&width=1167&top_left_y=761&top_left_x=479)


Because hydride ion is a base as well as a nucleophile, the actual nucleophilic acyl substitution step takes place on the carboxylate ion rather than on the free carboxylic acid and gives a high-energy dianion intermediate. In this intermediate, the two oxygens are complexed to a Lewis acidic aluminum species. Thus, the reaction is relatively difficult, and acid reductions require higher temperatures and extended reaction times.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0745.jpg?height=274&width=1138&top_left_y=1183&top_left_x=496)


Alternatively, borane in tetrahydrofuran $\left(\mathrm{BH}_{3} / \mathrm{THF}\right)$ is a useful reagent for reducing carboxylic acids to primary alcohols. Reaction of an acid with $\mathrm{BH}_{3} / \mathrm{THF}$ occurs rapidly at room temperature, and the procedure is often preferred to reduction with $\mathrm{LiAlH}_{4}$ because of its relative ease and safety. Borane reacts with carboxylic acids faster than with any other functional group, thereby allowing selective transformations such as that on p-nitrophenylacetic acid. If the reduction of $p$-nitrophenylacetic acid were done with $\mathrm{LiAlH}_{4}$, both the nitro and carboxyl groups would be reduced.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0745.jpg?height=253&width=957&top_left_y=1749&top_left_x=584)


Biological Conversions of Carboxylic Acids -

The direct conversion of a carboxylic acid to an acyl derivative by nucleophilic acyl substitution does not occur in biological chemistry. As in the laboratory, the acid must first be activated by converting the - OH into a better leaving group. This activation is often accomplished in living organisms by reaction of the acid with adenosine triphosphate (ATP) to give an acyl adenosyl phosphate, or acyl adenylate, a mixed anhydride combining a carboxylic acid and adenosine monophosphate (AMP, also known as adenylic acid). In the biosynthesis of fats, for example, a long-chain carboxylic acid reacts with ATP to give an acyl adenylate, followed by subsequent nucleophilic acyl substitution of a thiol group in coenzyme A to give the corresponding acyl CoA (FIGURE 21.7).


FIGURE 21.7 MECHANISM -

In fatty-acid biosynthesis, a carboxylic acid is activated by reaction with ATP to give an acyl adenylate, which undergoes nucleophilic acyl substitution with the -SH group on coenzyme A. (ATP $=$ adenosine triphosphate; $A M P=$ adenosine monophosphate.)
(1) ATP is activated by coordination to magnesium ion, and nucleophilic addition of a fatty acid carboxylate to phosphorus then yields a pentacoordinate intermediate...
(2... which expels diphosphate ion ( $\mathrm{PP}_{\mathrm{i}}$ ) as leaving group and gives an acyl adenosyl phosphate in a process analogous to a nucleophilic acyl substitution reaction.
(3) The -SH group of coenzyme A adds to the acyl adenosyl phosphate, giving a tetrahedral alkoxide intermediate . . .
(4)... which expels adenosine monophosphate (AMP) as leaving group and yields the fatty acyl CoA.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0746.jpg?height=366&width=727&top_left_y=500&top_left_x=935)


FIGURE 21.7 MECHANISM -


FIGURE 21.7 MECHANISM -

Pentacoordinate intermediate
(2)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0746.jpg?height=264&width=631&top_left_y=1467&top_left_x=885)


FIGURE 21.7 MECHANISM -

Acetyl adenosyl phosphate


(acyl adenylate) -


(acyl adenylate) -

Note that the first step in FIGURE 21.7-reaction of the carboxylate with ATP to give an acyl adenylate-is itself a nucleophilic acyl substitution on phosphorus. The carboxylate first adds to a $\mathrm{P}=\mathrm{O}$ double bond, giving a fivecoordinate phosphorus intermediate that expels diphosphate ion as a leaving group.


(acyl adenylate) - 21.4 Chemistry of Acid Halides


Preparation of Acid Halides -

Acid chlorides are prepared from carboxylic acids by reaction with thionyl chloride $\left(\mathrm{SOCl}_{2}\right)$, as we saw in the previous section. Similar reaction of a carboxylic acid with phosphorus tribromide ( $\mathrm{PBr}_{3}$ ) yields the acid bromide.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0747.jpg?height=117&width=438&top_left_y=641&top_left_x=556)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0747.jpg?height=115&width=434&top_left_y=642&top_left_x=1130)


Reactions of Acid Halides -

Acid halides are among the most reactive of carboxylic acid derivatives and can be converted into many other kinds of compounds by nucleophilic acyl substitution mechanisms. The halogen can be replaced by -OH to yield an acid, by -OCOR to yield an anhydride, by -OR to yield an ester, by $-\mathrm{NH}_{2}$ to yield an amide, or by R' to yield a ketone. In addition, the reduction of an acid halide yields a primary alcohol, and reaction with a Grignard reagent yields a tertiary alcohol. Although the reactions we'll be discussing in this section are illustrated only for acid chlorides, similar processes take place with other acid halides.
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Acid anhydride -


Acid anhydride -

Ketone


Acid anhydride -

Conversion of Acid Halides into Carboxylic Acids: Hydrolysis
Acid chlorides react with water to yield carboxylic acids. This hydrolysis reaction is a typical nucleophilic acyl substitution process and is initiated by attack of water on the acid chloride carbonyl group. The tetrahedral intermediate undergoes elimination of $\mathrm{Cl}^{-}$and loss of $\mathrm{H}^{+}$to give the product carboxylic acid plus HCl .
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0747.jpg?height=242&width=1250&top_left_y=1885&top_left_x=432)


Acid anhydride -

Because HCl is formed during hydrolysis, the reaction is often carried out in the presence of a base such as pyridine or NaOH to remove the HCl and prevent it from causing side reactions.


Conversion of Acid Halides into Anhydrides -

Nucleophilic acyl substitution reaction of an acid chloride with a carboxylate anion gives an acid anhydride. Both symmetrical and unsymmetrical acid anhydrides can be prepared.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0748.jpg?height=226&width=887&top_left_y=191&top_left_x=619)


Conversion of Acid Halides into Esters: Alcoholysis -

Acid chlorides react with alcohols to yield esters in a process analogous to their reaction with water to yield acids. In fact, this reaction is probably the most common method for preparing esters in the laboratory. As with hydrolysis, alcoholysis reactions are usually carried out in the presence of pyridine or NaOH to react with the HCl formed.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0748.jpg?height=324&width=1047&top_left_y=673&top_left_x=539)


The reaction of an alcohol with an acid chloride is strongly affected by steric hindrance. Bulky groups on either partner slow down the reaction considerably, resulting in a reactivity order among alcohols of primary > secondary > tertiary. As a result, it's often possible to selectively esterify an unhindered alcohol in the presence of a more hindered one. This can be important in complex syntheses in which it's sometimes necessary to distinguish between similar functional groups. For example,
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0748.jpg?height=459&width=1266&top_left_y=1229&top_left_x=424)


PROBLEM How might you prepare the following esters using a nucleophilic acyl substitution reaction of an 21-9 acid chloride?
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{CH}_{3}$
(b) $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$
(c) Ethyl benzoate


PROBLEM Which method would you choose if you wanted to prepare cyclohexyl benzoate-Fischer
21-10 esterification or reaction of an acid chloride with an alcohol? Explain.


Conversion of Acid Halides into Amides: Aminolysis -

Acid chlorides react rapidly with ammonia and amines to give amides. As with the acid chloride-plus-alcohol method for preparing esters, this reaction of acid chlorides with amines is the most commonly used laboratory method for preparing amides. Both monosubstituted and disubstituted amines can be used, but not trisubstituted amines ( $\mathrm{R}_{3} \mathrm{~N}$ ).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0749.jpg?height=587&width=1196&top_left_y=178&top_left_x=459)


Because HCl is formed during the reaction, two equivalents of the amine must be used. One equivalent reacts with the acid chloride, and one equivalent reacts with the HCl by-product to form an ammonium chloride salt. If, however, the amine component is valuable, amide synthesis is often carried out using one equivalent of the amine plus one equivalent of an inexpensive base such as NaOH . For example, the sedative trimetozine is prepared commercially by reaction of $3,4,5$-trimethoxybenzoyl chloride with the amine morpholine in the presence of one equivalent of NaOH .
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0749.jpg?height=375&width=1349&top_left_y=1035&top_left_x=388)


WORKED EXAMPLE 21.3 -


Synthesizing an Amide from an Acid Chloride -

How might you prepare $N$-methylpropanamide by reaction of an acid chloride with an amine?


Strategy -

As its name implies, $N$-methylpropanamide can be made by reaction of methylamine with the acid chloride of propanoic acid.


Solution -


Solution -

Propanoyl Methylamine N-Methylpropanamide chloride


Solution -

PROBLEM Write the mechanism of the reaction just shown between 3,4,5-trimethoxybenzoyl chloride and 21-11 morpholine to form trimetozine. Use curved arrows to show the electron flow in each step.


Solution -

PROBLEM How could you prepare the following amides using an acid chloride and an amine or ammonia?
21-12 (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONHCH}_{3}$
(b) $N, N$-Diethylbenzamide
(c) Propanamide


Conversion of Acid Chlorides into Alcohols: Reduction and Grignard Reaction -

Acid chlorides are reduced by $\mathrm{LiAlH}_{4}$ to yield primary alcohols. The reaction is of little practical value, however, because the parent carboxylic acids are generally more readily available and can themselves be reduced by $\mathrm{LiAlH}_{4}$ to yield alcohols.