(Reactions) Carboxylic Acids

Carboxylic acids can be synthesized from primary alcohols via the use of:

strong oxidizing agent (KMnO₄, H₂CrO₄, CrO₃/H₂SO₄ (Jone’s reagent))

Carboxylic acids can be synthesized from alkyl halides, using ________ ________ and ________, followed by an acid workup.

Grignard reagent, and CO₂

Carboxylic acid derivatives:

amide, ester, acid anhydride, acid halide

The relative reactivity of carboxylic acid derivatives is correlated with the:

stability of their leaving group.

The most reactive carboxylic acid derivative is:

acid halide

Carboxylic acid derivatives react via:

nucleophilic acyl substitution

Fischer esterification converts a carboxylic acid into an ________ in the presence of an ________ and a strong acid catalyst.

ester; alcohol.

Ester can be converted back into a carboxylic acid by reacting it with:

aqueous acid

Saponification can convert ________ into carboxylic acid, in the presence of ________.

ester; NaOH.

Two Grignard reagents can react with an acid chloride, acid anhydride, or ester to form a:

tertiary alcohol

LiAlH₄ is a strong reducing agent that reduces esters and acid chlorides to:

alcohols.

LiAlH₄ can reduce amides to:

amines.

DIBAL-H is a mild reducing agent that, at low temperatures, can reduce ________ to an aldehyde.

ester

LTBA is a mild reducing agent that can reduce ______ _______ to an aldehyde.

acid chloride

Primary amide reacted with molecular bromine (Br₂) and hydroxide (OH-) produces:

primary amine

An alkyl halide reacting with a cyanide ion produces:

nitrile (C-N triple bond)

Nitriles can be reduced to primary amines with:

LiAlH₄ (lithium aluminum hydride)

In nitrile hydrolysis reactions, nitrile reacts with aqueous acid and heat to produce:

carboxylic acid

A nitrile reacting with a Grignard reagent, followed by an acid workup, produces a:

ketone

Hydrogen cyanide (HCN) can react with an aldehyde or ketone to form a:

cyanohydrin