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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

Write structural formulas for the following compounds

  1. methyl isopropyl ether (b) di-iso-butyl ether (c) 2-methoxyoctane

(d) diallyl ether (e) allyl ethyl ether (f) cycloheptane oxide

(g) trans-2,3-epoxyheptane (h) (2R,3S)-2-ethoxypentan-3-ol (i) cis-2,3-dimethyloxirane

Rank the given solvents in decreasing order of their ability to dissolve each compound

(a) HCOO-Na+

(b)

(c)


Solvents

Ethyl ether, water, ethanol, dichloromethane

Show how the following ethers might be synthesized using (1) alkoxymercuration-demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)

  1. 2-methoxybutane
  2. Ethyl cyclohexyl ether
  3. 1-methoxy-2-methylcyclopentane
  4. 1-methoxy-1-methylcyclopentane
  5. 1-isopropoxy-1-methylcyclopentane
  6. Tert-butyl phenyl ether

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

Question. (A true story.) An inexperienced graduate student moved into a laboratory and began work. He needed some diethyl ether for a reaction, so he opened an old, rusty 1-gallon can marked 鈥渆thyl ether鈥� and found there was half a gallon left. To purify the ether, the student set up a distillation apparatus, started a careful distillation, and went to the stockroom for the other reagents he needed. While he was at the stockroom, the student heard a muffled 鈥渂oom鈥�. He quickly returned to his lab to find a worker from another laboratory putting out a fire. Most of the distillation apparatus was embedded in the ceiling.

(a) Explain what probably happened.

(b) Explain how this near disaster might have been prevented.
See all solutions

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