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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 chiral BINAP ligand shown in figure 8-8 contains no asymmetric carbon atoms. Explain how this ligand is chiral.

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)

Propose a mechanism to show how 3,3-dimethylbut-1-ene reacts with dilute aqueous H2SO4to give 2,3-dimethylbutan-2-ol and a small amount of 2,3-dimethylbut-2-ene.

One of the principal components of lemongrass oil is limonene, . When limonene is treated with excess hydrogen and a platinum catalyst, the product is an alkane of formula . What can you conclude about the structure of limonene?

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
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