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Chapter 5: Q.5 (page 180)

A molecule is achiral if it has a plane of symmetry in any conformation. Each of the following conformations does not have a plane of symmetry, but rotation around a carbon–carbon bond forms a conformation that does have a plane of symmetry. Draw this conformation for each molecule.

a.

b.

Short Answer

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a.

b.

Step by step solution

01

Plane of symmetry

The term "plane of symmetry" refers to an imaginary plane that divides a molecule into two equal/identical halves.

02

Achiral molecules

The molecules that are superimposable with their corresponding mirror images are termed achiral.

Achiral molecules possess a plane of symmetry.

03

Rotation around carbon-carbon bonds

a. A rotation around the carbon-carbon bond ( and ) yields a conformer of the molecule that has a plane of symmetry.

Conformer of a

b. The rotation about the carbon-carbon ( and ) bond by yields the conformer that possesses a plane of symmetry.

Conformer of b

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Most popular questions from this chapter

Which compounds are meso compounds?

a.

b.

c.

Drawn are four isomeric dimethylcyclopropanes.

a. How are the compounds in each pair related (enantiomers, diastereomers, constitutional isomers): A and B; A and C; B and C; C and D?

b. Label each compound as chiral or achiral.

c. Which compounds, alone, would be optically active?

d. Which compounds have a plane of symmetry?

e. How do the boiling points of the compounds in each pair compare: A and B; B and C; C and D?

f. Which of the compounds are meso compounds?

g. Would an equal mixture of compounds C and D be optically active? What about an equal mixture of B and C?

Rank the following groups in order of decreasing priority?

a.-COOH,-H,-NH2,-OH

b.-CH2CH3,-CH3,-H,-CH(CH3)2

c.-H,-CH3,-Cl,-CH2Cl

d.-CH=CH2,CH3,C≡CH,-H

Draw all possible stereoisomers for each compound. Label pairs of enantiomers and diastereomers.

a.

b.

c.

The amino acid (S)-alanine has the physical characteristics listed under the structure.

a. What is the melting point of (R)-alanine?

b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?

c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine?

d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine?

e. Label each of the following as optically active or inactive: a solution of pure (S)-alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.
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