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of acid chlorides into carboxylic acids, esters, amides, or anhydrides (Figure 15 09) These cyclic compounds are named lactones and lactams, respectively

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Cyclic amides (Lactams) Lactams are named similar to lactones above

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Nitriles can also be named as derivatives of carboxylic acids by replacing the –ic A cyclic ester is called a lactone (the Cyclic amide are called lactams

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vibrations known as "amide bands," e g , amide I, amide II, etc The amide I stretching mode, at 3420 cm -\, cyclic amides have a band in the range 3220- 3170

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Carboxylic Acid Derivatives: Nucleophilic Acyl

Substitution ReactionsSubstitution

Reactions

(Nitriles are treated as acid derivatives as they have similar reactivity.) Com p ounds containin g g rou p are called nitriles:pg gp • Simple open-chain nitriles are named by adding -nitrileas a suffix to the alkane

names, with the nitrile carbon numbered C1;• Nitriles can also be named as derivatives of carboxylic acids by replacing the

ic acidor -oic acidending with -onitrile, or by replacing the -carboxylic acidending with -carbonitriles;

• The nitrile carbon is attached to C1 carbon.

18-1

Naming Carboxylic Acid DerivativesAcid halidesare named by identifying first the acyl group and then the halide;

the acyl group name is derived from the carboxylic acid name by replacing the ic acid or the acid name by replacing the ic acid or the -carboxylic acidending with -ylor -carbonyl, respectively.O Cl pentanoyl chlorideS y mmetric anh y dridesandc y clic anh y dridesare named b y re p lacin g the word 18-2 yy yy yp g acidwithanhydride; unsymmetrical anhydridesare named by citing the two acid alphabetically and then addinganhydrides.

Naming Carboxylic Acid DerivativesEstersare named by first identifying the alkyl group attached to the oxygen and then the

carboxylic acid, with the -ic acidreplaced with-ate. A cyclic ester is called a lactone(the common name); the systematic name is oxa-2-cycloalkanone. -valerolactone (systematic: 5-methyloxa-2- cyclopentanone) -propiolactone (systematic: oxa-2-cyclobutanone)-butyrolactone

(systematic: oxa-2-cyclopentanone)Amidesare named by replacing the -ic acidor -oic acidending with -amide, or by rep-

lacing the -carboxylic acidending with -carboxamide. Cyclic amide are called lactams (the common name); the systematic name is aza-2-cycloalkanones. llt 18-3 -va l ero l ac t am (systematic: aza-2- cyclohexanone)

Spectroscopy of Carboxylic Acid Derivatives

18-4

Nucleophilic Acyl Substitution Reactions

Tetrahedron

intermediate

Greater resonance, shorter C- L bond

18-5

Factoids of Acid Derivatives

tthi f fCO s t re t c hi ng f requency o f C O

Two bands corresponding

Rotational activation

energy E a = 88 kJ mol -1 Two bands corresponding to symmetric and asymmetric stretching motions a

Greatly help

Acid derivatives are both basic and acidic

Greatly

help stabilize the protonated species

Relative reactivity:

electronic effectelectronic effect 18-6 Relative Reactivity of Carboxylic Acid Derivatives steric effect

Interconversion

diagram 18-7

Acyl Substitution Reactions of Acid Halides

A s acid halides are most reactive among all acid derivatives, all these reaction could happen with the acid halides.

Recall preparation:Recall

preparation: 18-8

Acyl Substitution Reactions of Acid Halides

Hydrolysis:

Base is needed to neutralized the HCl formed.

Alcoholysis:

1 o alcohol (l hi d d d

Alcoholysis:

(l ess hi n d ere d an d more reactive) Ai li 2 o alcohol (more hindered and less 1 o and 2 o amines can be used, but not 3 o amines A m i no l ys i s: (more hindered and less reactive) Two equivalents of amine are used due to the HCl formation. 18-9

Reactions of Acid Halides

When the amine isWhen

the amine is valuable, 1 eq. of NaOH can be added in addition to 1 eq. of the amine.

Reduction: hydride

substitution-addition

The modified LAH reacts

with acid chloride faster than

Modified

LAH: with the resulting aldehyde.

Reaction of

diorganocopper

With G i d

diorganocopper reagent happens only with acid halides; but not with carboxylic id t id With G r i gnar d

Reagent:

18-10 ac id s, es t ers, am id es, or acid anhydrides.

With Gilman

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