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Chapter 1: Problem 63

Which of the following compounds will have a meso isomer also? (a) 2 -Bromo \(-3\) -chlorobutane (b) \(2,3-\) Dichloropentane (c) 2 -Hydroxy butanoic acid (d) 2, 3 -Dibromobutane

Short Answer

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(a) 2-Bromo-3-chlorobutane (b) 2,3-Dichloropentane (c) 2-Hydroxybutanoic acid (d) 2,3-Dibromobutane Answer: (b) 2,3-Dichloropentane and (d) 2,3-Dibromobutane have meso isomers.

Step by step solution

01

(a) 2-Bromo-3-chlorobutane

2-Bromo-3-chlorobutane has two stereocenters at carbons 2 and 3. However, there is no plane of symmetry in this molecule, therefore it doesn't have a meso isomer.
02

(b) 2,3-Dichloropentane

2,3-Dichloropentane has two stereocenters at carbons 2 and 3. To have a meso isomer, it must have a plane of symmetry when one stereocenter has R and the other one has S configuration. In this case, 2,3-Dichloropentane does have a plane of symmetry when one stereocenter has R and the other one has S configuration, so it has a meso isomer.
03

(c) 2-Hydroxybutanoic acid

2-Hydroxybutanoic acid has only one stereocenter at carbon 2, so it cannot have a meso isomer as a meso compound requires more than one stereocenter.
04

(d) 2,3-Dibromobutane

2,3-Dibromobutane has two stereocenters at carbons 2 and 3. To have a meso isomer, it must have a plane of symmetry when one stereocenter has R and the other one has S configuration. In this case, 2,3-Dibromobutane does have a plane of symmetry when one stereocenter has R and the other one has S configuration, so it has a meso isomer. In conclusion, compounds (b) 2,3-Dichloropentane and (d) 2,3-Dibromobutane have meso isomers.

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Most popular questions from this chapter

When (-) lactic acid is treated with methanol under acidic conditions, (+) methyl lactate, an ester, is obtained as the product. Has the configuration at chiral centre changed?

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