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Chapter 15: Q35. (page 570)

Question: What is the major monobromination product formed by heating each alkane with Br2 ?


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Step by step solution

01

Monobromination

The organic reaction involving the replacement of the most reactive C-H bond by a bromide ion forming a C-Br bond in the presence of thermal energy is known as the monobromination reaction.

02

Product

Let us consider the bromination of the given alkanes,

a) In 3-ethylhexane, the hydrogen bonded to the tertiary carbon atom is replaced by a bromide ion. This is because of the relative stability of the tertiary carbon and the reactivity of the C-H bond.


Formation of 3-bromo,3-ethylhexane

b) In methyl cyclopropane, the hydrogen atom bonded to the only tertiary carbon atom is replaced to give the following major product.

Formation of bromo-substituted methyl cyclopropane


c) In 2,2-dimethyl butane, the most reactive hydrogen bonded to the secondary carbon atom is replaced by bromide ion.


Formation of 2-bromo,3,3-dimethyl butane

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Most popular questions from this chapter

Question: Classify each radical as Primary , secondary or tertiary carbon radicals .

Question: a. What product(s) (excluding stereoisomers) are formed when Y is heated with Cl2 ?

b. What product(s) (excluding stereoisomers) are formed when Y is heated with Br2?

c. What steps are needed to convert Y to the alkene Z?

Question: The triphenylmethyl radical is an unusual persistent radical present in solution in equilibrium with its dimer. For 70 years the dimer was thought to be hexaphenylethane, but in 1970, NMR data showed it to be A.

a. Why is the triphenylmethyl radical more stable than most other radicals?

b. Use curved arrow notation to show how two triphenylmethyl radicals dimerize to form A.

c. Propose a reason for the formation of A rather than hexaphenylethane.d. How could 1 H and 13C NMR spectroscopy be used to distinguish between hexaphenylethane and A?

Question: Explain why radical bromination of p-xylene forms C rather than D.

Devise a synthesis of 1-methylcyclohexene oxide from methylcyclohexane. You may use any other required organic or inorganic reagents
See all solutions

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