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Chapter 5: Q.72 (page 212)

Label each compound as chiral or achiral. Compounds that contain a single carbon common to two rings are called spiro compounds. Because carbon is tetrahedral, the two rings are perpendicular to each other.

a.

b.

c.

d.

Short Answer

Expert verified
  1. Achiral
  2. Chiral
  3. Achiral
  4. Chiral

Step by step solution

01

Chiral and Achiral compounds

  • A compound that consists of an ‘asymmetrical center’ such that its mirror images are ‘non-superimposable’ is named a chiral compound.
  • The compounds which ‘do not contain any asymmetrical center’ and whose mirror images are ‘superimposable’ are named achiral compounds.
02

Axial chirality

Axial chirality: The axis which bisects a tetrahedral molecule in a manner such that the groups around the chiral axis are non-identical or different is termed chiral axis.

Secondly, the compound possessing a chiral axial is said to exhibit axial chirality.

03

Predicting the chirality of the given compounds

a.

Compound a

The given compound is achiral as it does not contain any chiral center nor a chiral axis.

b.

Chiral axis in compound b

The given compound is chiral as it consists of a chiral axis.

c.

Compound c

The given compound is achiral as it does not contain any chiral center nor a chiral axis.

d.

Compound d

The given compound is chiral as it contains a chiral center (indicated using the asterisk symbol).

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Most popular questions from this chapter

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?

Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopenatane.

  1. How do the boiling points of A and B compare? What about A and C?
  2. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C.
  3. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?

A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of water. What is the specific rotation of this compound?

Locate the stereogenic centers in each Newman projection and label each center as R or S.

a.

b.

Saquinavir (trade name Invirase) is a protease inhibitor, used to treat HIV (human immunodeficiency virus).

  1. Locate all stereogenic centers in saquinavir, and label each stereogenic center as R and S.
  2. Draw the enantiomer of saquinavir.
  3. Draw a diastereomer of saquinavir.
  4. Draw a constitutional isomer that contains at least one different functional group.
See all solutions

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