Chapter 18 - Functional Derivatives of Carboxylic Acids

Lactams

________ are cyclic amides with an acyl carbon and a N atom in the ring.

Lactones

________ are cyclic esters that include the acyl carbon and the O atom.

Acid

________ can catalyze the reaction with weaker nucleophiles, in which case the acyl O atom is protonated first.

tetrahedral intermediate

The ________ collapses due to the loss of a leaving group and the reformation of the C "The op bond.

hydrolysis of esters

The ________ and amides requires acid or base, although acid halides and acid anhydrides need not.

Esters

________ and HCl are formed when acid chlorides combine with alcohols.

HO2

________ is a powerful enough nucleophile to attack the ester or amide carbonyl directly.

Anions

________ that are more stable are better ________ leaving groups.

Amides

________ are insufficiently reactive to react with alcohols.

Imides

________ are significantly more acidic than amides due to the delocalization of the negative charge of the N- deprotonated anion over both carbonyls.

Two acyl groups

________ are linked to an O atom in an acid anhydride.

acyl group

A(n) ________ is linked to a halogen, commonly Cl, in acid halides.

Nitriles

________ are named by replacing- oic acid of the parent acid with- onitrile.

N bond

________ has a partial double bond nature and a significant rotation barrier.

N atom

The ________ in amides is sp2 hybridized as a result of a third important resonance contributing structure that forms a double bond between the acyl C and ________.

term Nitriles

The ________ refer to having a cyano group bonded to carbon.

carboxylic acid

In the presence of an acid catalyst, esters react with water to form a(n) ________ and alcohol.

Acid chlorides

________ react with two equivalents of ammonia and one equivalent each of 1° and 2° amines to generate an amide and one equivalent of ammonium chloride.

imide anion

Because the ________ is stabilized by delocalization of the negative charge onto the two carbonyl oxygens, imides are more acidic than amides.

sulfonamide anion

The ________ is stabilized by negative charge delocalization onto the two O atoms.

electrophilic acyl carbon

A strong nucleophile adds straight to the ________, causing the C bond to break "O p bond is formed, resulting in a tetrahedral carbonyl addition intermediate.

Imides

________ are distinguished from amides by the presence of two acyl groups connected to the same N atom.

Esters

________ combine with alcohols in an acid- catalyzed reaction termed transesterification, an equilibrium process in which one ________.

N atom

If the ________ has one or two groups attached to it, the groups are called after the designator N,- and the parent acid's- ic acid is substituted by- amide.

ester

When the ________ is acid- sensitive, a base such as a tertiary amine is utilized to neutralize the HCl as it forms.

Imides

________ (pKa 8- 10) dissolve in aqueous NaOH by forming water- soluble sodium salts, as shown in the image attached.