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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

1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol.

(a)Show what alcohol will undergo condensation, with loss of water, to give 1,4-dioxane.

(b)Propose a mechanism for this reaction

An acid-catalyzed reaction was carried out using methyl cellosolve (2-methoxyethanol) as the solvent. When the 2-methoxyethanol was redistilled, a higher-boiling point fraction (bp 162oC) was also recovered. The mass spectrum of this fraction showed the molecular weight to be 134. The IR and NMR spectrum are shown here. Determine the structure for this compound and propose a mechanism for its formation.

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Show how you would use a protecting group to convert 4-bromobutan-1-ol to hept-5-yn-1-ol.

Question. Predict the major products of the following reactions, including stereochemistry where appropriate.

  1. 2,2-dimethyloxirane +(oxygen-labelled water)
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