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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

Predict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark.

(a)

(b)

(c)

When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 掳C, an interesting Diels鈥揂lder adduct of the formula C20H14results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and a broad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings of anthracene reacted as a diene.

Phenol reacts with three equivalents of bromine in CCl4(in the dark) to give a product of formula C6H3OBr3. When this product is added to bromine water, a yellow solid of molecular formula C6H2OBr4 precipitates out of the solution. The IR spectrum of the yellow precipitate shows a strong absorption (much like that of a quinone) around 1680cm-1 . Propose structures for the two products.

Phenolphthalein, a common nonprescription laxative, is also an acid-base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.

(a) Propose a mechanism for the synthesis of phenolphthalein.

(b) Propose a mechanism for the conversion of phenolphthalein to its red dianion in the base.

(c) Use resonance structures to show that the two phenolic oxygen atoms are equivalent (each with half a negative charge) in the red phenolphthalein dianion.


Phthalic anhydride Phenolphthalein red dianion

The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Diels鈥揂lder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.
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