ORGANIC CHEMISTRY 3540

ALDEHYDES & KETONES

NUCLEOPHILIC ADDITION

REVIEW.

NUCLEOPHILIC ADDITION, GENERAL.

REACTIVITY.

NUCLEOPHILIC ADDITION, SPECIFIC

HYDRATION.

RATE OF REACTION IS VERY SLOW IN PURE WATER BUT FAST IN BASE OR ACID. WHY? MECHANISM!

NUCLEOPHILIC ADDITION OF ALCOHOLS TO FORM ACETALS.

MECHANISM.

NUCLEOPHILIC ADDITION OF PRIMARY AMINES, RNH₂, TO FORM IMINES.

SIMPLE CHEMICAL TEST

DEMONSTRATION.

OXIMES, SEMICARBAZONES, AND 2,4-DINITROPHENYLHYDRAZONES (2,4-DNP'S) ARE USED AS DERIVATIVES TO IDENTIFY ALDEHYDES AND KETONES.

MECHANISM.

WOLFF-KISHNER REDUCTION.

GRIGNARD REACTIONS.

GRIGNARD PLUS FORMALDEHYDE GIVES PRIMARY ALCOHOLS

GRIGNARD PLUS OTHER ALDEHYDES GIVES SECONDARY ALCOHOLS

GRIGNARD PLUS KETONES GIVES TERTIARY ALCOHOLS

NOTE: ALCOHOLS CAN BE CONVERTED TO ALKYL HALIDES (HOW?) WHICH CAN BE CONVERTED TO GRIGNARDS WHICH CAN MAKE NEW ALCOHOLS, ETC.

NOTE: YOU CANNOT MAKE A GRIGNARD OF A REAGENT WHICH CONTAINS ACID GROUPS (CO₂H, OH, NH₂) OR CARBONYL (C=O) GROUPS!.

SYNTHESIZE 2-PROPANOL, 1-PROPANOL AND 1-BUTANOL STARTING FROM COMPOUNDS CONTAINING NO MORE THAN TWO CARBON ATOMS.