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Chapter 11: Q46P (page 588)

Show how you would convert (S)-heptan-2-ol to

(a) (S)-2-chloroheptane.

(b) (R)-2-bromoheptane.

(c) (R)-heptan-2-ol.

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

(a): Alcohol

Alcohol is a compound that contains a hydroxyl group. It is used in the spirits.

Heptan-2-ol is used as a flotation agent for the processing of ore. TheHydroxyl group is attached to the second carbon of the heptane compound.

02

Conversion

(S)-Heptan-2-ol is treated with SOCl2 to form (S)-2-chloroheptane.

Formation of (S)-2-chloroheptane

03

(b): Reagents

TsCl is used in treating primary alcohol as an activating group, and pyridine neutralizes hydrochloric acid generated from the reaction.

04

Conversion

(S)-Heptan-2-ol is treated with TsCl/pyridine forms (S)-heptane-2-tosylate, which on further reaction with forms (R)-2-bromoheptane.

Formation of (R)-2-bromoheptane

05

(c): Reagents role

TsCl is used in treating primary alcohol as an activating group, and pyridine neutralizes hydrochloric acid generated from the reaction.

06

Conversion

(S)-Heptan-2-ol is treated with TsCl/pyridine forms (S)-heptane-2-tosylate, which, on further reaction with sodium hydroxide, kept in the cold to avoid elimination and forms (R)-heptan-2-ol.

Formation of (R)-hepatan-2-ol

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Most popular questions from this chapter

Show how you would accomplish the following synthetic conversions

(a)

(b)

(c)

(d)

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.

Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxy-chloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychlorides much like it reacts with tosyl chloride (Section 11-5), displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.

The following pseudo-syntheses (guaranteed not to work) exemplify a common conceptual error.

(a)What is the conceptual error implicit in these syntheses?

(b)Propose syntheses that are more likely to succeed.

Give the structures of the intermediates and products V through Z.
See all solutions

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