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Chapter 10: PROBLEM 10.56 (page 423)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

Step by step solution

01

Stability of carbocation  

Carbocations are the intermediates formed in the addition reaction of alkenes.

The stability order of carbocations is 3°>2°>1°.

02

1,2-hydrogen shift

The stability of carbocations is the reason for 1,2-hydrogen shift. After the shift of hydrogen to the adjacent position, the carbocation is generated, which is more stable.

03

Explanation

The reaction of the given compound with HBr proceeds via 1,2-hydrogen shift to generate a 3°carbocation. The 3°carbocation forms a tertiary halide product.

The mechanism is shown below:

Reaction mechanism

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Most popular questions from this chapter

Question: How many degrees of unsaturation are present in each compound?

  1. C6H6
  2. role="math" localid="1648637368534" C8H18
  3. C7H8O
  4. C7H11Br
  5. C5H9N

Question: Label the alkene in each drug as E or Z. Enclomiphene is one component of the fertility drug Clomid. Tamoxifen is an anticancer drug. Clavulanic acid is sold in combination with the antibiotic amoxicillin under the trade name Augmentin.

a

b.

c.

Question: Draw the products formed when (CH3)2C=CH2 is treated with each reagent.

a. HBr

b.H2O, H2SO4

c. CH3CH2HO,H2SO4

d. Cl2

e.Br2 ,H2O

f. NBS (aqueous DMSO)

g. [1] BH3; [2] H2O2 ,HO-

Question: How many rings and π bonds does a compound with molecular formula C10H14 possess? List all possibilities.

Question: What stereoisomers are formed when pent-1-ene is treated with H2O and H2SO4?
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