Chem 335 - Winter 2000
Organic Chemistry II
Dr. Carl C. Wamser

Chapter 15 Skills

Knowledge - Level 1

know the terminology:

acetal, hemiacetal, ketal, hemiketal
alpha-carbon, deuterium exchange
cyanohydrin, Wittig reagent, ylid, 1,3-dithiane
imine, oxime, hydrazone
haloform, Baeyer-Villager oxidation
Clemmensen reduction, Wolff-Kishner reduction
McLafferty rearrangement

Concepts - Level 2

understand how the polarity of the carbonyl group leads to nucleophilic addition reactions

recognize how acid or base catalysis assists nucleophilic addition reactions

recognize the relative reactivity expected for aldehydes or ketones
(steric hindrance / conjugation effects)

Applications - Level 3

be able to name various aldehydes and ketones

write products of oxidation or reduction reactions involving aldehydes or ketones

recognize appropriate reagents to carry out a specific reaction

write products of nucleophilc additions to carbonyl compounds:

water --> hydrates
alcohols --> hemiacetals, acetals
thiols --> thioacetals or 1,3-dithianes
amines --> imines
hydrides --> alcohols
organometallics --> larger alcohols (with a new C-C bond)
Wittig reagents --> alkenes

Analytical Skills - Level 4

write mechanisms for nucleophilic addition reactions, with acid or base catalysis

write mechanisms for alpha-substitution or enol reactions

Synthetic Skills - Level 5

create a synthetic sequence to prepare a given target molecule