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Chapter 25: 67 (page 1046)

Devise at least three different methods to prepare N-methylbenzylamine PhCH2NHCH3from benzene, any one-carbon organic compounds, and any required reagents.

Short Answer

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Methods to prepare N-methylbenzineamine from benzene

Step by step solution

01

Introduction of an alkyl chain on the benzene ring

It is done by the electrophilic aromatic substitution on the benzene ring. An electrophile attacks one of the hydrogen atoms on the benzene ring to form a substituted benzene ring.

02

Introduction of the amine group in the alkyl chain

The carbon chain is attacked with a base to introduce a leaving group into the carbon chain. An amine group is introduced to the carbon chain by direct reaction with either of NH3 or alkylic amine compound.

03

Methods to prepare N-methylbenzineamine from benzene

As many as five methods to prepare N-methylbenzineamine from benzene are shown hereunder.

Methods to prepare N-methylbenzineamine from benzene

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Most popular questions from this chapter

Question: Draw a structure corresponding to each name.

a. 2,4-dimethylhexan-3-amine

b. N-methylpentan-1-amine

c. N-isopropyl-p-nitroaniline

d. N-methylpiperidine

e. N,N-dimethylethanaminef. 2-aminocyclohexanoneg. N-methylanilineh. m-ethylaniline

Question: Draw the product formed when each compound is treated with NaNO2 and HCl.

a.

b.

c.

d.

Heating compound X with aqueous formaldehyde forms Y \(\left( {{{\bf{C}}_{{\bf{17}}}}{{\bf{H}}_{{\bf{23}}}}{\bf{NO}}} \right)\),which has been converted to a mixture of lupinine and epilupinine, alkaloids isolated from lupin, a perennial ornamental plant commonly seen on the roadside in parts of Alaska (Section 25.10). Identify Y and explain how it is formed.

Synthesize each compound from benzene. Use a diazonium salt as one of the synthetic intermediates.

Question: Heating compound X with aqueous formaldehyde forms Y (C17H23NO),which has been converted to a mixture of lupinine and epilupinine, alkaloids isolated from lupin, a perennial ornamental plant commonly seen on the roadside in parts of Alaska (Section 25.10). Identify Y and explain how it is formed.
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