W16: ACID CHLORIDE, ACID ANHYDRIDES, AND ESTERS

An _________________ is a carboxylic acid derivative in
which the —OH portion of the carboxyl group, has been replaced with a —Cl atom.

acid chloride

Draw the general formula of acid chloride

answer:

Naming acid chlorides:

• Replace the -ic acid ending of the common name of the parent carboxylic
  acid with _____________.

• -yl chloride

Naming acid chlorides:

• Replace the -oic acid ending of the IUPAC name of the parent carboxylic acid with _______________.

• -oyl chloride

Preparation of an acid chloride from its parent carboxylic acid involves reacting the acid with one of several ____________

inorganic chlorides

Give the three inorganic chloride:

1.) PCI3
2.) PCI5
3.) SOCI2

Acid chlorides react rapidly with water, in a _________________, to regenerate the parent carboxylic acid.

hydrolysis reaction

______________ are useful starting materials for the synthesis of other carboxylic acid derivatives, particularly _______ and __________.

1.) Acid chlorides
2.) esters
3.) amides

Synthesis of esters and amides using acid chlorides is a ________________ process than ester and amide synthesis using a carboxylic acid.

more efficient

An ____________ is a carboxylic acid derivative in which the -OH portion of the carboxyl group has been replaced with carbon atom double-bonded to an oxygen atom (C=O) and single-bonded to another oxygen atom (C-O).

acid anhydride

Draw the general formula of acid anhydride:

Answer:

Structurally, acid anhydrides can be visualized as two carboxylic acid molecules bonded together after ________________ from the acid molecules.

removal of a water molecule

____________________ both R groups are the same) are named by replacing the acid ending of the parent carboxylic acid name with the word anhydride.

Symmetrical acid anhydrides

_______________ (different R groups present) are named by using the names of the individual parent carboxylic acids (in alphabetic order) followed by the word anhydride.

Mixed acid anhydrides

In general, acid anhydrides _________________ by directly reacting the parent carboxylic acids together.

cannot be formed

Instead, an _____________ is reacted with a _______________ to produce the acid anhydride.

1.) acid chloride
2.) carboxylate ion

Like acid chlorides, acid anhydride cannot exist in biological systems, as they undergo __________ to regenerate the parent carboxylic acids.

hydrolysis

Reaction of an ________ with an acid anhydride is a useful method for synthesizing esters.

alcohol

Inorganic acid such as ____________, _____________, and ___________ react with alcohols to form esters in a manner similar to that for carboxylic acids.

1.) sulfuric acid
2.) phosphoric acid
3.) nitric acids

A ____________ is an organic compound formed by reaction of an alcohol with phosphoric acid.

phosphate ester

What are the three biologically important phosphoric acid that exist?

1.) phosphoric acid
2.) diphosphoric acid
3.) triphosphoric acid

_________________, the simplest of the three acids, undergoes intermolecular dehydration to produce diphosphoric acid.

Phosphoric acid

Phosphoric acid, the simplest of the three acids, undergoes ______________ to produce diphosphoric acid.

intermolecular dehydration

Another intermolecular dehydration, involving diphosphoric acid and phosphoric acid produces ________________.

triphosphoric acid

All three phosphoric acids undergo esterification reactions with alcohols, producing species such as:

1.) Diphosphate monoester
2.) Triphosphate monoester

Draw carboxylic acid anhydride

answer:

Draw diphosphoric acid:

Answer: