Organic Enols and Enolate Ion Reactions

All carbonyl atoms with at least one BLANK atom are in equilibrium with their respective BLANK

alpha-hydrogen, enol tautomers

The rate of interconversion of tautomers is accelerated by

trace acid or base

What are the reactive hot spots on aldehydes and ketones

carbonyl carbon, alpha carbon

Identify the mechanism

nucleophilic addition to a carbonyl

identify the mechanism

deprotonation of alpha carbon

a hydrogen atom on a sp³ carbon atom alpha to a carbonyl group is BLANK times more acidic than a hydrogen atom on a sp3 carbon atom on a hydrocarbon

30

Bases such as alkoxide ions produce BLANK but strong bases convert carbonyls into BLANK

small amounts of enolates of carbonyls, their enolates

What are 3 examples of strong bases that produce enolates from carbonyls?

LDA, [(CH₃)₂CH]₂N^-Li⁺, and NaH

identify the mechanism

halogenation of nucleophilic alpha carbon on carbonyl

identify the mechanism

aldol condensation

what time of reaction is aldol reaction

dimerization

Aldehydes are BLANK reactive than ketones for BLANK reasons

more, steric and electronic

How to predict the product of an unknown aldol/claisen reaction

1. write formula for anion of component with most acidic alpha hydrogen

2. write formula for product that would form following attack on carbonyl group of other component (addition or substitution)

Enols are BLANK nucleophilic than enolate ions

less

Enols may act as nucleophiles towards reactive electrophiles such as

halogens or protonated carbonyl groups

Deuterium exchange happens to alpha carbons when using a

deuterated solvent

base catalyzed dehydration of an aldol product produced what

alpha, beta - unsaturated carbonyl compounds (lose one oxygen)

identify the mechanism

claisen condensation

What is CH₃I commonly used for in reactions with enols?

alkylation of the alpha carbon

Bonded carbonyl groups after deprotonation of an alpha carbon will act as a BLANK at the BLANK

nucleophile, negatively charged carbon

The solvent 1,2-dimethoxyethane plays what role in enol reactions

dissolves enolate salts and shields spectator cations

identify the mechanism

alkylation of enolate ions via alkyl halides

When should a claisen condensation be considered?

When the carbonyl is an ester

identify the mechanism

acid catalyzed enolization of ketones

acid catalyzed enolization results in what in a final product

an alkene

identify the mechanism

base catalyzed aldol reaction

identify the mechanism

iodoform reaction

what does a