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Unsymmetrical Molecules

Edexcel AS-level ChemistryAlkenesLesson 12 of 19

When a hydrogen halide adds to an unsymmetrical alkene, such as propene, the H can join either carbon of the C=C, so two different products are possible:

CH3CH=CH2 + HBr → CH3CHBrCH3 (major) or CH3CH2CH2Br (minor)

2-bromopropane is the major product and 1-bromopropane is the minor product. The reason lies in the carbocation formed in step 1.

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Key terms in this lesson

carbocation
A positively charged carbon ion formed when a carbon atom loses a share in a bonding pair of electrons.
inductive effect
The shifting of electron density along a chain of bonded atoms due to differences in electronegativity, such as electron release by alkyl groups.

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