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Chapter 25: Q44P (page 1031)

Synthesize Novocine from benzene and any other reagents of four carbons or fewer.

Short Answer

Expert verified

Mechanism of the reaction given in details.

Step by step solution

01

Fridel craft:

Friedel craft in thepresence of solvent benzene gives toluene.

02

Nitrotoluene

Nitrotoluene is prepared from toluene by the addition of mixed acid HNO3and H2SO4.

03

Oxidation by KMnO4

Para nitro toluene is oxidised to give paranitrobenzoic acid.

04

SOCl2 addition

05

Substitution of Cl group

Addition ofOHCH2CH2NEt3

06

Product formation

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Most popular questions from this chapter

Question. Section 17-12 showed how nucleophilic aromatic substitution can give aryl amines if there is a strong electron-withdrawing group ortho or para to the site of substitution. Consider the following example.


(a) Propose a mechanism for this reaction.
(b) We usually think of fluoride ion as a poor leaving group. Explain why this reaction readily displaces fluoride as the leaving group.
(c) Explain why this reaction stops with the desired product, rather than reacting with another dinitrofluorobenzene.

Question. Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.



  1. Propose a mechanism for the acetylation of pyrrole just shown. You may begin with pyrrole and the acylium ion,. Be careful to draw all the resonance structures of this intermediate.
  2. Explain why pyrrole reacts more readily than benzene, and also why substitution occurs primarily at the 2-position rather than 3-position.

Question: Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.

(a) pentan-1-amine

(b) N-methylbutan-1-amine

(c) N-ethyl-N-propylbutan-2-amine

(d) N-benzylpropan-1-amine

(e)



(f) 3-propylaniline

(g) 4-isobutylaniline

Question. The alkaloid coniine has been isolated from hemlock and purified. Its molecular formula is. Treatment of coniine with excess methyl iodide, followed by silver oxide and heating, gives the pure (S)-enantiomer of N,N-dimethyloct-7-ene-4-amine. Propose a complete structure for coniine, and show how this reaction gives the observed product.

Question: Show how you can synthesize the following tertiary amine three different ways, each using a different secondary amine and adding the final substituent by

  1. reductive amination (3 ways)
  2. acylation-reduction (3 ways)

See all solutions

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