Carboxylic Acids, Cyclic Carboxylic Acid Derivatives, and Nitrogen-Containing Compounds

MCAT Prep: Organic Chemistry Part 4

4.5

Carboxylic acids have pK_a values around _____ due to resonance stabilization of the conjugate base.

increase

Electronegative atoms ________ acidity with inductive effects

higher

Boiling point is ________ than alcohols because of the ability to form two hydrogen bonds

oxidation

? of primary alcohols with KMnO₄

soap; micelles

formation of ______ by reacting carboxylic acids with NaOH; arrange in ________

Nucleophilic acyl substitution

Nu - nucleophile

X - OH

reduction to alcohols

H-AlH₃Li⁺ = H^-

OEt = OH

CH₃ = R

carboxylic acid

What is number 1?

aldehyde

What is number 2?

alcohol

What is number 3?

Decarboxylation

What mechanism is this?

Keto form; more

What is the final product? Is it more or less stable?

Lactams

cyclic amides that are named according to the carbon atom bonded to the nitrogen

Beta-lactams

contain a bond between the beta-carbon and the nitrogen

Gamma-lactams

contain a bond between the gamma-carbon and the nitrogen

Lactones

cyclic esters that are named not only based on the carbon bonded to the oxygen, but also the length of the carbon chain itself

Amide

Imine

Enamine

Azide

Nitrile

Isocyanate

Strecker Synthesis

Reagents: aldehyde, ammonium chloride (NH₄Cl), potassium cyanide (KCN)

Strecker synthesis part 1

Aminonitrile formation

Strecker synthesis part 2

Hydrolysis

Gabriel (Malonic-Ester) Synthesis

Reagents: potassium phthalamide, diethyl bromomalonate

Gabriel Synthesis