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 Bra Br trans-but-2-ene Meso product Brz Me Me Me Me cis-but-2-ene Racemic product -....in ior 4. Make a model and draw the structure of the cyclic bromonium ion that results from addition to cis-2-butene 5. Make a model of the structure of the racemic products that result from opening of this bromonium ion by an SN2 mechanism 6. For each enantiomeric structure assign the configuration at each centre

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 36AP
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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
Me
Bra
Me
H
trans-but-2-ene
Meso product
H
H
Bra
Me
Me
Me
Me
Me
Br
cis-but-2-ene
Racemic product
-..un ion
4. Make a model and draw the structure of the cyclic bromonium ion that results from
addition to cis-2-butene
5. Make a model of the structure of the racemic products that result from opening of
this bromonium ion by an Sn2 mechanism
6. For each enantiomeric structure assign the configuration at each centre
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 Me Bra Me H trans-but-2-ene Meso product H H Bra Me Me Me Me Me Br cis-but-2-ene Racemic product -..un ion 4. Make a model and draw the structure of the cyclic bromonium ion that results from addition to cis-2-butene 5. Make a model of the structure of the racemic products that result from opening of this bromonium ion by an Sn2 mechanism 6. For each enantiomeric structure assign the configuration at each centre
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