Halogenoalkanes

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Question 6
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Under suitable conditions, 2-bromohexane reacts with sodium hydroxide to produce a mixture of five organic products, A, B, C, D, and E.

Products A, B, and C are alkenes:

  • A is a structural isomer of B and C.
  • A does not exhibit stereoisomerism.
  • B and C are a pair of stereoisomers.

Products D and E are alcohols:

  • D and E are a pair of enantiomers.
1.

Give the names of the two concurrent mechanisms responsible for the formation of the alkenes and the alcohols.

  • Mechanism to form alkenes:
  • Mechanism to form alcohols:
[2]
2.

Define the term stereoisomers.

[1]
3.

Deduce the IUPAC name of isomer A. Explain why A does not exhibit stereoisomerism.

[2]
4.

Outline the mechanism for the reaction of 2-bromohexane with sodium hydroxide to form alkene A.

[3]
5.

Deduce the IUPAC name of isomer B and the name of isomer C. Explain the origin of the stereoisomerism in B and C.

[3]
6.

Draw 3D representations of enantiomers D and E to show how their structures are related.

[3]
7.

A student compares the rates of hydrolysis of 1-chlorohexane, 1-bromohexane, and 1-iodohexane. State and explain the order in which precipitates appear when these halogenoalkanes are reacted with aqueous silver nitrate.

[3]

Halogenoalkanes Questions

  1. A Level
  2. /Chemistry
  3. /Halogenoalkanes