1/31/10

OxidationReduction
Reactions
(Review)

Question

Reducing Agents

Which isomer of C4H10O can be prepared

by hydrogenation of a ketone?

Oxidizing Agents

A)

B)

C)

D)

Catalytic Hydrogenation

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Dissolving-Metal NH3 Reduction

Hydride Reductions

LiAlH4 is a stronger reducing agent than NaBH4

LiAlH4 is used to reduce compounds that are
nonreactive toward NaBH4

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Question

Question

Which one of the isomeric alcohols of

formula C5H12O can be prepared by LiAlH4
reduction of a ketone?

A) 1-pentanol

B) 2-methyl-2-butanol

C) 3-methyl-2-butanol

D) 2,2-dimethyl-1-propanol

Which of the esters shown, after reduction

with LiAlH4 and aqueous workup, will yield
two molecules of only a single alcohol?

A) CH3CH2CO2CH2CH3

B) C6H5CO2CH2C6H5

C) C6H5CO2C6H5

D) none of these

DIBAL allows the addition of one equivalent of hydride to

an ester

Formation of Amines by Reduction

NaBH4 can be used to selectively reduce an aldehyde or

a keto group in a compound

Question
Which one of the following cannot be
reduced by NaBH4?
A)

B)

C)

D)

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Oxidation of Alcohols

Oxidation of a Primary Alcohol

Question

Question

A)

B)

When 1-propanol is treated with

Na2Cr2O7/H2SO4 followed by treatment
with CH3OH, H2SO4 the product
isolated is:
A) propanal B) propanoic acid

C)

D)

C) propanol D) methyl propanoate

Treatment of 1-propanol with K2Cr2O7,

H2SO4, and heat will produce:

The oxidation of a primary alcohol can be stopped at the

aldehyde if pyridinium chlorochromate (PCC) is used
as the oxidizing agent

Question
What is the product of the reaction of 1butanol with PCC in CH2Cl2?

A)

B)

C)

D)

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Oxidation of Aldehydes and Ketones

Tollens Reagent Oxidizes Only

Aldehydes