Chapter 13 - Carboxylic Acid Derivatives Flashcards Preview

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Flashcards in Chapter 13 - Carboxylic Acid Derivatives Deck (8)
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1
Q

List the acid derivatives in order of increasing reactivity

A

Carboxylate < amides < COOH or esters < acid anhydride < acid chloride

acid chlorides are the best leaving group

2
Q

How does COOH form from a Grignard reagent?

A

the Grignard reagent will react with CO2 to form a carboxylate ion, which will get quenched to make COOH

3
Q

Fischer Esterificaton

A

COOH is treated with an acid to form an ester

4
Q

Saponification

Hydrolysis

A

An ester is treated with water to make COOH; can be done in acidic and basic conditions

5
Q

Which acid derivatives can be reduced by NaBH4?

Which can ONLY be reduced by LAH?

A

NaBH4 - acid chlorides and acid anhydries

LAH - esters, amides, and carboxylates

6
Q

Hoffman Rearrangement

A

an amide is treated with Br2 / NaOH to make an amine with ONE LESS carbon than the starting product (this is due to the carbonyl carbon being removed)

7
Q

Reduction can be stopped at the aldehyde level if the starting compound is ______. The reagent used to achieve this is called _____

A

ester, DIBAL

8
Q

In order to reduce and stop at the aldehyde level using LTBA, the starting compound must be a ____

A

acid chloride