Organic chemistry chapter 21

How does one produce a cyclic ester? (lactone)

reacting OH and COOH on the same molecule
Carboxylic acid and ammonia or primary amines form?
amides

How does one form a cyclic amide? (lactam)

NH2 and COOH on the same molecule react

What process makes nitriles into carboxylic acids?

Hydrolysis

List in order of increasing acidity?

Acid anhydrides

Acid

Acid Halides

Acid, Acid anhydrides, Acid Halides
What is the heirarchy for parent names?
Acid>ester>amide>nitrile>aldehyde>Ketone> alcohol> amine>Alkene>Alkyne

Tertiary amides have…

strong interactions, therefore high boiling points
How does the number of NH bonds effect the melting points of amides?
it increases them
Acid chlordies and anhydrides cannot be in what mediums? (why and what do they form?)
They can’t be in water or alcohol because they form esters due to their high reactivities
What are good polar aprotic solvents?
esters, tertiary amides, and nitriles

explain the interconversion of acid derivatives

A nucleophile adds to a carbonyl to form a tetrahedral intermediate, then the leaving group detaches reforming the carbonyl

To convert carboxylate to anything, what must first be done?
it must be reacted with SOCl2, because an acid chloride is so reactive it can be turned into any other derivative (i.e. anhydride, ester, or amine)
How does one form an anhydride?
reaction of an acid or carboxylate with a carbonyl.; Tetrahedral intermediate forms, and chloride ion leaves and H+ is abstracted.

Ester from acid chloride?

Add alcohol
Acid chloride to amide?

amide turns into amide plus+ (ex ammonia to primary amide, primary amide to secondary)

Anhydride to ester?
Alcohol attacks one C=O, C=O leaves and H+ is abstracted
Ester to amide

Nucleophile must be NH3 or primary amine, prolonged heating is necessary

explain transesterification
an alkoxy group can be replaced by another with an acid or base catalyst and a large excess of the preferred alcohol.
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