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Chapter 15: PROBLEM 15.11 (page 766)

Question: Predict the product(s) of light-initiated reaction with NBS in CCl4 for the following starting materials.

  1. cyclohexene
  2. 3,4-dimethylhex-3-ene

Short Answer

Expert verified

Answer

c.

Step by step solution

01

Bromination using NBS

For allylic bromination, a convenient bromine source is N-bromosuccinimide (NBS), a derivative of succinimide.

NBS is denser than carbon tetrachloride and is not very soluble in it.

02

Product from ethylbenzene

c. When ethylbenzene undergoes a light-initiated reaction with NBS in CCl4 , it forms the below product.

Ethylbenzene undergoes a light-initiated reaction with NBS inCCl4

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Most popular questions from this chapter

Question: When Br2 is added to buta-1,3- diene at -150C , the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at -600C, the product ratio is 10% A and 90% B.

a. Propose structures for products A and B (Hint: In many case, an allylic carbocation is more stable than a bromonium ion.)

b. Propose a mechanism to account for formation of both A and B.

c. Show why A predominates at -150C and B predominates at -600C .

d. If you had a solution of pure A, and its temperature were raised to -600C , what would you expect to happen ? Propose a mechanism to support your prediction.

Predict the products of the following Diels-Alder reactions.

a)

b)

c)

d)

In a strongly acidic solution, cyclohexa-1, 4-diene tautomerizes to cyclohexa-1, 3-diene. Propose a mechanism for this rearrangement, and explain why it is energetically favorable.

Question: The central carbon atom of an allene is a member of two double bonds, and it has an interesting orbital arrangement that holds the two ends of the molecule at right angles to each other.

  1. Draw an orbital diagram of allene, showing why the two ends are perpendicular.
  2. Draw the two enantiomers of penta-2,3-diene. A model may be helpful.

Propose a mechanism for each reaction, showing explicitly how the observed mixtures of products are formed.

a) 3-methyl-but-2-en-1-ol+HBr鈫�1-bromo-2-ene+3-bromo-3-methyl-1-ene

b)2-methyl-but-3-en-2a-ol+HBr鈫�1-bromo-2-ene+3-bromo-3-methyl-1-enec)cyclopenta-1,3-diene+Br2鈫�3,4-dibromocyclopent-1-ene+3,5-dibromocyclopent-1-ene

d)1-cholorobut-2-ene+AgNO3+H2O鈫�but-2-en-1-ol+but-3-en-2-ol

e)3-cholorobut-1-ene+AgNO3+H2O鈫�but-2-en-1-ol+but-3-en-2-ol
See all solutions

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