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Chapter 17: Q39P (page 892)

Show how you would synthesize the following compounds, using the indicated starting materials.

(a) 3-phenylbutan-1-ol from styrene

Short Answer

Expert verified

A chemical reaction in which one or more halogens (F, Cl, Br or I) are added to the compound getting halogenated is known as halogenation.

Step by step solution

01

Halogenation

A chemical reaction in which one or more halogens (F, Cl, Br or I) are added to the compound getting halogenated is known as halogenation.

02

Preparation of 3-phenylbutan-1-ol from styrene.

To synthesize 3-phenylbutan-1-ol from styrene, a halogenation process is done which is followed by substitution.

03

Preparation of 1-methoxy-4-(1-methoxyethyl)benzene from anisole.

For getting 1-methoxy-4-(1-methoxyethyl)benzene from anisole, halogenations are followed by the required substitution reaction as shown below.

04

Preparation of 2-(4-nitrophenyl)acetonitrile from toluene.

By treating toluene with nitric acid and then by halogenations followed by substitution of NaCN, 2-(4-nitrophenyl)acetonitrile is formed.

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Most popular questions from this chapter

Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.

Reagents Desired Product

(a) benzene + n-butyl bromide n-butylbenzene

(b) ethylbenzene + tert-butyl chloride p-ethyl-tert-butylbenzene

(c) bromobenzene + ethyl chloride p-bromoethylbenzene

(d) benzamide (PhCONH3) + CH3 CH2 CI p-ethylbenzamide

(e) toluene + HNO3, H2SO4 , heat 2,4,6-trinitrotoluene (TNT)

Indane can undergo free-radical chlorination at any of the alkyl positions on the aliphatic ring.

indane

  1. Draw the possible monochlorinated products from this reaction.
  2. Draw the possible dichlorinated products from this reaction.
  3. What instrumental technique would be most helpful for determining how many products are formed, and how many of those products are monochlorinated and how many are dichlorinated?
  4. Once the products have been separated, what instrumental technique would be most helpful for determining the structures of all the dichlorinated products?

The bombardier beetle defends itself by spraying a hot quinone solution from its abdomen (see photo). This solution is formed by the enzyme-catalyzed oxidation of hydroquinone by hydrogen peroxide. Write a balanced equation for this oxidation.

What products would you expect from the following coupling reactions?

(a)

(b)

(c)

(d)

(e)

When 1,2-dibromo-3,5-dinitrobenzene is treated with excess NaOH at 50 °C, only one of the bromine atoms is replaced. Draw an equation for this reaction, showing the product you expect. Give a mechanism to account for the formation of your proposed product.
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