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Chapter 18: Q19P (page 945)

Give the structures of the carbonyl compound and the amine used to form the following imines.

(a)

(b)

(c)

(d)

(e)

(f)

Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

(f)

Step by step solution

01

Imines

Ammonia or primary amine under proper conditions reacts with a ketone or an aldehyde to form an imine.

02

Mechanism of imine formation

The mechanism of imine formation is a type of acid catalyzed nucleophlic addition of an amine to the carbonyl group.The fist step is the attack of an amine to an aldehyde or ketone which is followed by deprotonation of the nirogen atom that gives an unstable intermediate known as the carbinolamine. Second step is the conversion of carbinolamine to imine by loss of a water molecule. The formation of imine is a reversible process and most imines can be hydrolysed back into the amines and aldehydes or ketones.

03

Structures of carbonyl compound and the amine

(a)

(b)


(c)

(d)

(e)

(f)

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Most popular questions from this chapter

Show how Wittig reactions might be used to synthesize the following compounds. In each case, start with an alkyl halide and a ketone or an aldehyde.

(a)

(b)

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The following road-map problem centers on the structure and properties of A, a key intermediate in these reactions. Give structures for compounds A through J.

Show how you would synthesize each compound from starting materials containing no more than six carbon atoms.

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(b)

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Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.

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