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Organic chemistry chapter 21
Organic chemistry review for Carboxylic Acid Derivatives
19
Chemistry
Undergraduate 2
07/24/2008

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Term

How does one produce a cyclic ester? (lactone)

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

How does one form a cyclic amide? (lactam)

Definition
NH2 and COOH on the same molecule react
Term

What process makes nitriles into carboxylic acids?

Definition
Hydrolysis
Term

List in order of increasing acidity?

Acid anhydrides

Acid

Acid Halides

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

Tertiary amides have...

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

explain the interconversion of acid derivatives

Definition

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

Term
To convert carboxylate to anything, what must first be done?
Definition
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)
Term
How does one form an anhydride?
Definition
reaction of an acid or carboxylate with a carbonyl.  Tetrahedral intermediate forms, and chloride ion leaves and H+ is abstracted.
Term

Ester from acid chloride?

Definition
Add alcohol
Term
Acid chloride to amide?
Definition

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

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

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

Term
explain transesterification
Definition
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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