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Chapter 8: Q19Q (page 395)

Propose a mechanism for the addition of bromine water to cyclopentene, being carefulto show why the trans product results and how both enantiomers are formed.

Short Answer

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first step is addition of a bromine molecule to cyclopentene ring to form bromonium ion.

Step by step solution

01

Step 1:

first step is addition of a bromine molecule to cyclopentene ring to form bromonium ion.

02

 

Now water molecule is added in the second step. Here two possibilities occur due to the presence of bromonium ion. first if water attack from the back side (dash bond) then bromine come upward (wedge bond) while if water molecule attack from the front side(wedge bond) then bromine go backward(dash bond). The two products formed are enantiomers as the only difference in orientation of the bromine atom and hydroxyl group

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Most popular questions from this chapter

The two butenedioic acids are called fumaric acid(trans) and maleic acid(cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how would you convert

  1. Fumaric acid to (卤)-tartaric acid.
  2. Fumaric acid to meso-tartaric acid.
  3. Maleic acid to (卤)-tartaric acid.
  4. Maleic acid to meso-tartaric acid.

Predict the carbenoid addition products of the following reactions.

(a) trans-hex-3-ene+ CH2I2, Zn(Cu)

(b) ciz-hept-2-ene+ CH2I2, Zn(Cu)

(a) When HBr adds across the double bond of 1,2-dimethylcyclopentene, the product is a mixture of the cis and trans isomers. Show why this addition is not stereospecific.

(b) When 1,2 dimethylcyclopropene undergoes hydroboration oxidation, one diastereomer of the product predominantes. Show why this addition is stereospecific, and predict the stereochemistry of the major product.

In the hydroboration of 1-methylcyclopentene shown in Solved Problem 8-3, the reagents are achiral, and the products are chiral. The product is a racemic mixture of trans-2-methylcyclopentanol, but only one enantiomer is shown. Show how the other enantiomer is formed.

Question: Show how you would accomplish the following synthetic conversions.

  1. 3-methylpent-2-ene to 2-chloro-3-methylpentan-3-ol
  2. Chlorocyclohexane to trans-2-chlorocyclohexaol
  3. 1-methylcyclopentanol to 2-chloro-1-methylcyclopentanol
See all solutions

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