Ochem_CH17_Alcohols

Reduction of Aldehyde

Reduction of Ketones

Reduction of Esters

Reduction of Carboxylic Acids

Addition to Carbonyl

Addition to Carbonyl

Addition to Carbonyl

Addition to Carbonyl

Preparation - Markovnikov

Preparation: Non-Markovnikov

Preparation: Expoxide

Preparation: Hydroxylation


Dehydration: Tertiary

Dehydration: Secondary and Tertiary

Oxygenation: Primary Alcohols

Oxygenation: Primary Alcohols

Oxygenation: Secondary Alcohols

Oxidation of Phenols: Fremy's Salt

More Fremy's Salt

Tertiary Alkyl Halide

Alkyl Halide from primary or secondary

Another alkene to alcohol, Mark

Another alkene to cis diol

What functional groups are reduced to a primary alcohol?

A ketone is reduced to a ____ alcohol.

NaBH4 does not reduce ___ or ___

What are two products of a conjugated carbonyl and NaBH4?

LiAlH4 is ____ reactive than NaBH4.

LiAlH4 reacts explosively with ___ and ___. It uses ___ ____ solvents instead

The nucleophile in NaBH4 and LiAlH4 is___. It attacks the ____ group and creates a ____ intermediate.

What are the incompatible functional groups for Grignard addition resulting in alcohols? Why?

Tosylate review p.359

Dehydration of an alcohol to an alkene is what kind of a reaction? What kind of intermediate does it involve?
Review this mechanism.

Dehydration of 2nd and tertiary alcohol with ____ in ___ is what kind of reaction? Review this mechanism.

Oxidation of a primary alcohol yields ____.

Oxidation of a secondary alcohol yields ___

Oxidation of a tertiary alcohol yields ____.

What are four common oxidizing agents for alcohols? Which is the weakest?

PCC oxidizes a primary alcohol to what? The other 3 yield what?

All 4 oxidizers yield what from a secondary alcohol?

What do all 4 oxidizers yield with a tertiary alcohol?

The 4 oxidizers apply to what kind of carbons?

Review Jones' mechanism

What is used to "protect" alcohols?

R-OH + TMS-Cl yields what? What is it stable to? What cleaves it?

Addition of a Grignard reagent to formaldehyde yields a ____; to an aldehyde yields a ___; to a ketone or an ester yields a ___.

Alcohols are often "protected" by the formation of ___.

Alcohols can be ___ to give alkenes by treatment with ___ and can be transformed into alkyl halides by treatment with ___ or ___.

Alcohols are ___ acidic with pKa of about ___ and react with ___ bases and alkali metals to form ___.

Perhaps the most important reaction of alcohols is their ___ to carbonyl compounds.

Primary alcohols are oxidized to ___ , secondary to ___, and tertiary to ___.

___ is in ___ is often used for ___ primary alcohols to ___ and secondary alcohols to ___.

A solution of ___ in ___ is frequently used for ___ primary alcohols to ___ and secondary alcohols to ___.

In a phenol, substitution of the aromatic ring by an EWG ___ acidity.

Phenols can be ___ to ___ with Fremy's salt which can be reduced to ___ by reaction with ___.