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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

Complete the following proposed acid –base reactions, and predict whether the reactants or products are favored.

Question. Using any necessary reagents, show how you would accomplish the following syntheses.

Question: Several additional amine synthesies are effectively limited to making primry amines. The reduction of azides and nitro compounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds one carbon atom. Show how these amines syntheses can be used for the following conversions.
(a) allyI bromide → allylamine
(b) ethylbenzene → p-ethylaniline
(c) 1-bromo- 3-phenylheptane → 3-phenylheptan- 1-amine
(d) 1 -bromo- 3-phenylheptane → 4-phenyloctan- 1-anime

Question. A chemist is summoned to an abandoned waste-disposal site to determine the contents of a leaking, corroded barrel. The barrel reeks of an overpowering fishy odor. The chemist dons a respirator to approach the barrel and collect a sample, which she takes to her laboratory for analysis.

The mass spectrum shows a molecular ion at m/z101, and the most abundant fragment is at m / z86. The IR spectrum shows no absorptions above 3000 cm-1, many absorptions between 2800 and 3000 cm-1, no absorptions between 1500 and 2800 cm-1, and a strong absorption at 1200 cm-1. The proton NMR spectrum shows a triplet
(J = 7 HZ ) at 2.4, with integrals of 17 spaces and 11 spaces, respectively.

  1. Show what structural information is implied by each spectrum, and propose a structure for the unknown toxic waste.
  2. Current EPA regulations restrict the disposal of liquid wastes because they tend to leak out of their containers. Propose an inexpensive method for converting this waste to a solid, relatively odorless form for reburial.
  3. Suggest how the chemist can remove the fishy smell from her clothing.

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
See all solutions

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