(Reactions) Aldehyde and Ketone

Oxidation is a reaction that increases:

bonds to oxygen.

C-C single bonds cannot be broken during oxidation, therefore __________ alcohols cannot be oxidized.

tertiary

A primary alcohol reacting with a weak oxidizing agent produces:

aldehyde

A primary alcohol or aldehyde reacting with a strong oxidizing agent produces:

carboxylic acid

A secondary alcohol reacting with a strong OR weak oxidizing agent produces:

ketone

Weak oxidizing agents

PCC or

Swern oxidation (1. DMSO, (COCl)₂ 2. NEt₃)

Strong oxidizing agents

KMnO₄ or

H₂CrO4 (Chromic acid) or

CrO₃/H₂SO₄ (Jone’s reagent)

A ketone reacting with a weak or strong reducing agent, followed by an acid workup, produces:

secondary alcohol

An aldehyde reacting with a strong OR weak reducing agent, followed by an acid workup, produces:

primary alcohol

Weak reducing agent

NaBH₄ (Sodium borohydride)

Strong reducing agent

LiAlH₄ / LAH (lithium aluminum hydride)

An ester reacting with a strong reducing agent (LiAlH₄), followed by an acid workup, produces:

primary alcohol

A carboxylic acid reacting with a strong reducing agent, followed by an acid workup, produces:

primary alcohol

An ester or carboxylic acid reacting with a weak reducing agent (NaBH₄), followed by an acid workup, produces:

no reaction

An aldehyde reacting through Clemmensen reduction produces:

alkane

A ketone reacting through Clemmensen reduction produces:

alkane

An aldehyde reacting through Wolff-Kishner reduction produces:

alkane

A ketone reacting through Wolff-Kishner reaction produces:

alkane

Reagents for Clemmensen reduction: (2)

Zn(Hg) (amalgamated zinc)
HCl

Reagents for Wolff-KIshner reduction: (2)

(H₂NNH₂) (hydrazine)
KOH/heat

An aldehyde reacting with an alcohol in basic conditions produces:

hemi-acetal

A ketone reacting with an alcohol in basic conditions produces:

hemi-ketal

An aldehyde reacting with an alcohol in acidic conditions, followed by an acid workup, produces:

acetal

A ketone reacting with an alcohol in acidic conditions, followed by an acid workup, produces:

ketal

An acetal/ketal can be converted back into an aldehyde/ketone with:

H₃O+ (aqueous acid)

Imines and enamines can be converted back into ketones when reacted with:

catalytic acid in water

(cat. H+
H₂O)

Hydrolysis of an imine or enamine in the presence of water leads to the formation of:

a ketone

Grignard reagents contain a __________ atom inserted between a carbon and halogen (Cl, Br, I).

magnesium (Mg)

Grignard reagent can be formed by reacting a _______ _______ with Mg in an _______ solvent.

alkyl halide; aprotic solvent

Aprotic solvent (for Grignard reagent)

THF or Et₂O

The partial negative charge on carbon allows the Grignard reagent to function as a:

carboanion (very strong nucleophile)

An aldehyde reacting with a Grignard reagent, followed by an acid workup, produces:

secondary alcohol

A ketone reacting with a Grignard reagent, followed by an acid workup, produces:

tertiary alcohol

In the presence of water, a Grignard reagent will perform an acid-base reaction, producing:

alkane

Water is what kind of solvent?

protic

Protic sovents contain:

hydrogen directly bonded to O or N

3 components of a Wittig reagent:

1. PPh₃

2. Alkyl halide

3. n-BuLi (strong base)