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Chapter 25: PROBLEM 25.25 (page 1024)

Question: Devise a synthesis of each compound from aniline (C6H5NH2)

a.

b.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Conversion reaction

  • Convert the amine (aniline) into an amide (acetanilide) by the reaction with the acyl chloride.
  • Carry out the Friedel–Crafts reaction.
  • Hydrolyze the amide to generate the free amino group.
02

Explanation

a. The first step of the reaction involves acylation by the donation of electrons from the amine group.

In the second step, the Friedel–Craft alkylation reaction gives the alkyl group on the para position.

The third step proceeds via the hydrolysis.

Reaction of aniline to form a.

b.The first step of the reaction involves acylation of the amine group.

In the second step, the Friedel–Craft acylation reaction gives the acyl group on the ortho position.

The third step proceeds via the hydrolysis.

Reaction of aniline to form b.

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Most popular questions from this chapter

Draw a stepwise mechanism for each reaction.

Question: LSD (a hallucinogen) and codeine (a narcotic) are structurally more complex derivatives of 2-phenylethanamine. Identify the atoms of 2-phenylethanamine in each of the following compounds.

a.

b.

Answer the following questions about benzphetamine, a habit-forming diet pill sold under the trade name Didrex

  1. Label the stereogenic center(s).
  2. What amide(s) can be reduced to form benzphetamine?
  3. What carbonyl compound and amine can be used to make benzphetamine by reductive amination? Draw all possible methods.
  4. What products are formed by Hofmann elimination from benzphetamine? Label the major product.

Draw the products formed when p-methylaniline ( p-C6H4NH2) is treated with each reagent.

  1. HCl
  2. CH3COCl
  3. CH3CO2O
  4. Excess CH3I
  5. CH32C=O
  6. CH3COCl,AlCl3
  7. CH3CO2H
  8. NaNO2,HCl
  9. Part (b), thenCH3COCl,AlCl3
  10. CH3CHO,NaBH3CN

Decide which N atom in each molecule is most basic and draw the product formed when each compound is treated with CH3CO2H. Zolpidem (trade name Ambien) is used to treat insomnia, whereas aripiprazole (trade name Abilify) is used to treat depression, schizophrenia, and bipolar disorders.

(a)

(b)
See all solutions

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