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Chapter 14: Q 46P (page 748)

Show how you would convert 2-bromocyclohexanol to the following diol. You may use any additional reagents you need.

Short Answer

Expert verified

Different steps involved in the conversion process are as given below.

(1) Protection of hydroxyl group by treating 3-bromocyclohexanol withtriisopropylsilyl chloride(TIPSCl) in presence of triethylamine.

(2) Making Grignard reagent by treating the initial product with magnesium and ether.

(3) Reaction of Grignard reagent with a ketone (butan-2-one).

(4) Hydrolysis ( becomes OH).

(5) Removing the protection by reacting with tetrabutylammonium fluoride (Bu4N+F-). This gives the final product as diol.

Step by step solution

01

Steps involved in conversion of 2-bromocyclohexanol to the given diol

Different steps involved in the conversion process are as given below.

(1) Protection of hydroxyl group by treating 3-bromocyclohexanol withtriisopropylsilyl chloride(TIPSCl) in presence of triethylamine.

(2) Making Grignard reagent by treating the initial product with magnesium and ether.

(3) Reaction of Grignard reagent with a ketone (butan-2-one).

(4) Hydrolysis ( becomes OH).

(5) Removing the protection by reacting with tetrabutylammonium fluoride (Bu4N+F-). This gives the final product as diol.

02

Synthesis

conversion of 3-bromocyclohexanol to diol

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Most popular questions from this chapter

Question. Grignard reactions are often limited by steric hindrance. While Grignard reagents react in high yield with ethylene oxide and monosubstituted epoxides, yields are often lower with disubstituted epoxides. Tri- and tetrasubstituted epoxides react with difficulty, if at all.

(a) Show how to make these alcohols by a Grignard reacting with an epoxide.

(b) These alcohols cannot be made by a Grignard plus an epoxide. Show the reagents that would be required and why that reaction would be unlikely to succeed.

Give the expected products of the following reactions. Include a protonation step where necessary.

  1. 1,2-dimethyloxirane + isopropylmagnesium bromide
  2. ethyl oxide + n-butyllithium
  3. cyclohexyloxirane + ethyllithium

One of the crowning achievements of natural products synthesis was Bryostatin 1, published by Professor Gary Keck (University of Utah; Journal of the American Chemical Society,2011, 133, 744-747). The Bryostatins are a family of compounds isolated from aquatic invertebrates known as Bryozoans. The compounds are of interest for a variety of biological effects, including anti-cancer activity and reversing brain damage in rodents.

a. How many ether functional groups are present in Bryostatin 1?

b. Identify the other oxygen-containing functional groups.

c. This is called a macrolide because it contains a large number of atoms in the large ring. How many atoms are in the large ring?

d. How many chiral centers are in this molecule?

e. Using the number of chiral centers you reported in part (d), calculate the number of stereoisomers possible at these chiral centers. (Ignore stereoisomers at double bonds.)

Question. The following reaction resembles the acid-catalyzed cyclization of squalene oxide. Propose a mechanism for this reaction.

Propose a Williamson synthesis of 3-butoxy-1,1-dimethylcyclohexane from 3,3-dimethyl-cyclohexanol and butan-1-ol.
See all solutions

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