Carboxylic Acid Derivatives and Phosphorus-Containing Compounds

MCAT Prep: Organic Chemistry Part 5

three

Carboxylic acid derivatives contain ______ bonds to heteroatoms (O, N, halides, and so forth).

nucleophilic acyl substitution

Carboxylic acid derivatives can be interconverted through _____________ by swapping leaving groups.

descending

Carboxylic acid derivatives can be ranked based on _________ reactivity:

• acyl halides

• anhydrides

• carboxylic acids and esters

• amides

Acyl halides

are the most reactive carboxylic acid derivatives

Amides

are the least reactive carboxylic acid derivatives

down

A reaction that proceeds ______ the order of reactivity can occur spontaneously by nucleophilic acyl substitution

up

A reaction that proceeds ________ the order of reactivity requires special catalysts and specific reaction conditions

Anhydride synthesis with 2 carboxylic acids

Intramolecular formation of a cyclic anhydride

ortho-phthalic acid

Phthalic anhydride

anhydride

Amide formation from ?

ester

Amide formation from ?

Hydrolysis (acid)

? of an amide (what does it require?)

Amine

amide is reduced to ?

Transesterification

Hydrolysis

? of esters

Reduction

? of esters

Saponification

? of esters

Triacylglycerol

Glycerol

Soap

Phosphoric acid

a phosphate group or inorganic phosphate (P_i)

inorganic phosphate

At physiologic pH, ____________ includes both hydrogen phosphate (HPO₄^2-) and dihydrogen phosphate (H₂PO₄^-)

Pyrophosphate

(PP_i) is P₂O₇^4-, which is released during the formation of phosphodiester bonds in DNA

unstable; two

Pyrophosphate is _________ in aqueous solution, and is hydrolyzed to form _____ molecules of inorganic phosphate

Organic phosphates

nucleotides with phosphate groups, such as ATP, GTP, and those in DNA