11 The mechanism of bromination of an alkene, which involves a cyclic bromonium ion, explains why trans-2-butene and cis-2-butene give rise, respectively, to a meso structure and a racemic mixture of 2,3-dibromobutanes Me Brz Me Me Br trans-but-2-ene Meso product Bra Me Me cis-but-2-ene Racemic product 1. Make a model and draw the structure of the cyclic bromonium ion that results from addition to trans-2-butene 2. Make a model of the meso structure that results from opening of this bromonium ion by an SN2 mechanism 3. Assign the configuration at each centre of the structure you have drawn

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11
The mechanism of bromination of an alkene, which involves a cyclic bromonium ion,
explains why trans-2-butene and cis-2-butene give rise, respectively, to a meso structure
and a racemic mixture of 2,3-dibromobutanes
X
Me
Brz
Me
Me
Br
trans-but-2-ene
Meso product
Bra
Br
Me
Br
Me
cis-but-2-ene
Racemic product
1. Make a model and draw the structure of the cyclic bromonium ion that results from
addition to trans-2-butene
2. Make a model of the meso structure that results from opening of this bromonium ion
by an Sn2 mechanism
3. Assign the configuration at each centre of the structure you have drawn
Transcribed Image Text:11 The mechanism of bromination of an alkene, which involves a cyclic bromonium ion, explains why trans-2-butene and cis-2-butene give rise, respectively, to a meso structure and a racemic mixture of 2,3-dibromobutanes X Me Brz Me Me Br trans-but-2-ene Meso product Bra Br Me Br Me cis-but-2-ene Racemic product 1. Make a model and draw the structure of the cyclic bromonium ion that results from addition to trans-2-butene 2. Make a model of the meso structure that results from opening of this bromonium ion by an Sn2 mechanism 3. Assign the configuration at each centre of the structure you have drawn
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