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Chapter 20: Q18P c. (page 1065)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Short Answer

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(c)

Step by step solution

01

 Synthesis of N, N-dimethylformamide(DMF)

(c) When aniline is treated with acetic acid CH3COOH, an acetate ion is formed along with a phenyl ammonium ion. Further, on heating, acetanilide is formed.

02

Reaction of N, N-dimethylformamide(DMF)

Synthesis of N,N-dimethylformamide(DMF)

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Most popular questions from this chapter

Question:

  1. Why do most long-chain fatty acids show a large peak in the mass spectrum at m/z 60 ?
  2. Use equations to explain the prominent peaks at m/z 74 and m/z 87 in the mass spectrum of 2-methylpentanoic acid.
  3. Why doesn’t the mass spectrum of 2-methylpentanoic acid show a large peak at m/z 60 ?

Tributylin hydride (Bu3SnH)is used synthetically to reduce alkyl halides, replacing a halogen atom with hydrogen. Free-radical initiators promote this reaction, and free-radical inhibitors are known to slow or stop it. You job is to develop a mechanism, using the following reaction as an example.

The following bond-dissociation enthalpies may be helpful:

(a) Propose initiation and propagation steps to account for this reaction.

(b) Calculate values of ΔH for your proposed steps to show that they are energetically feasible. (Hint: A trace of Br2 and light suggests it’s there only as an initiator, to create Brradicals. Then decide which atom can be extracted most favorably from the starting materials by the Brradical. That should complete the initiation. Finally, decide what energetically favored propagation steps will accomplish the reaction).

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

(a)hex-1-yne

(b)hex-2-yne

(c)cis-hex-2-ene

(d)trans-hex-2-ene

(e)1,1-dibromohexane

(f)2,2-dibromohexane

(g)pentanal, CH3CH2CH2CH2CHO

(h)pentan-2-one, CH3-CO-CH 2CH2 CH3

(i) (+/)-3,4-dibromohexane

(j)meso-butan-2,3-diol

(k)2-methylhex-3-yn-2-ol

Question: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

b)

Question: Propose a mechanism for conversion of the dianion to the ketone under mildly acidic conditions.
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