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Oxidation–Reduction
Reactions

(Review)

Reducing Agents
Question
•  Which isomer of C4H10O can be prepared
by hydrogenation of a ketone?

•  A) B)

•  C) D)

Oxidizing Agents
Catalytic Hydrogenation

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Dissolving-Metal NH3 Reduction

LiAlH4 is a stronger reducing agent than NaBH4

Hydride Reductions
LiAlH4 is used to reduce compounds that are
nonreactive toward NaBH4

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Question Question
•  Which one of the isomeric alcohols of •  Which of the esters shown, after reduction
formula C5H12O can be prepared by LiAlH4 with LiAlH4 and aqueous workup, will yield
reduction of a ketone? two molecules of only a single alcohol?
•  A) 1-pentanol •  A) CH3CH2CO2CH2CH3
•  B) 2-methyl-2-butanol •  B) C6H5CO2CH2C6H5
•  C) 3-methyl-2-butanol •  C) C6H5CO2C6H5
•  D) 2,2-dimethyl-1-propanol •  D) none of these

Formation of Amines by Reduction

DIBAL allows the addition of one equivalent of hydride to
an ester

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
•  When 1-propanol is treated with
•  Treatment of 1-propanol with K2Cr2O7, Na2Cr2O7/H2SO4 followed by treatment
H2SO4, and heat will produce: with CH3OH, H2SO4 the product
isolated is:
•  A) B) •  A) propanal B) propanoic acid

•  C) D) •  C) propanol D) methyl propanoate

The oxidation of a primary alcohol can be stopped at the

aldehyde if pyridinium chlorochromate (PCC) is used Question
as the oxidizing agent
•  What is the product of the reaction of 1-
butanol with PCC in CH2Cl2?

•  A) B)

•  C) D)

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Oxidation of Aldehydes and Ketones

Tollens Reagent Oxidizes Only
Aldehydes