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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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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: Draw the structure of the four allylic halides formed when 3-methylcyclohexene undergoes allylic halogenation with NBS + hν.

Question: In cells, vitamin C exists largely as its conjugate base X. X is an antioxidant because radicals formed in oxidation processes abstract the labeled H atom, forming a new radical that haltsoxidation. Draw the structure of the radical formed by H abstraction, and explain why this Hatom is most easily removed.

Question:Draw all the monochlorination products that are formed from (S,S)-1,2-dimethylcyclopropane.

Question: Show all steps and reagents needed to convert cyclohexane into each compound: (a) the two enantiomers of trans-1,2-dibromocyclohexane; and (b) 1,2-epoxycyclohexane.

Question: Rank the following radicals in order of increasing stability.
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