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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: Which alkyl halides can be prepared in good yield by radical halogenation of an alkane?

Question:Draw the products formed in each reaction and include the stereochemistry around any stereogenic centers.

a.

b.

c.

d.

Question: Draw all constitutional isomers formed when each alkene is treated with NBS + hν.

a.

b.

c.

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

Question: Reaction of (CH3 )3 CH with Cl2 forms two products: (CH3 )2 CHCH2Cl (63%) and (CH3)3 CCl (37%). Why is the major product formed by cleavage of the stronger 1° C-H bond?
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