Problem

For each of the compounds described by the following names, 1. draw a three-dimensi...

For each of the compounds described by the following names,

1. draw a three-dimensional representation.

2. star (*)each chirality center.

3. draw any planes of symmetry.

4. draw any enantiomer.

5. draw any diastereomers.

6. label each structure you have drawn as chiral or achiral.

(a) (S)-2-chlorobutane

(b) (R)-1,1,2-trimethylcyclohexane

(c) (2R,3S)-2,3-dibromohexane

(d) (1R,2R)-1,2-dibromocyclohexane

(e) meso-hexane-3,4-diol,CH3CH2CH(OH)CH(OH)CH2CH3

(f) (;)-hexane-3,4-diol

Step-by-Step Solution

Solution 1

(a)

The three dimensional structure of (S)-2-chlorobutane is as follows:

If the carbon atom is attached to the four different groups or atoms, then that carbon is known as chiral carbon or chiral center. Here, the compound has one chiral center and it is represented with star as follows:

This compound doesn’t have a plane of symmetry because it contains a chiral carbon.

Enantiomers are non-superimposable mirror images. Thus, the enantiomer of this compound is as follows:

This compound has one stereogenic center but diastereomers should have two stereogenic centers. Thus, the compound (S)-2-chlorobutane doesn’t exhibit any diastereomers.

The compounds which have the chiral carbon atoms are as follows:

(b)

The structure of (R)-1,1,2-trimethylcyclohexane is as follows:

If the carbon atom is attached to the four different groups or atoms, then that carbon is known as chiral carbon or chiral center. Here, the compound has one chiral center and it is represented as follows:

This compound doesn’t have a plane of symmetry because it contains a chiral carbon.

Enantiomers are non-superimposable mirror images. Thus, the enantiomer of this compound is as follows:

This compound has one stereogenic center but diastereomers should have two stereogenic centers. Thus, the compound (R)-1,1,2-trimethylcyclohexane doesn’t exhibit any diastereomers.

The compounds which have the chiral carbon atoms are as follows:

(c)

The structure of (2R,3S)-2,3-dibromohexane is as follows:

If the carbon atom is attached to the four different groups or atoms, then that carbon is known as chiral carbon or chiral center. Here, the compound has two chiral centers and it is represented as follows:

This compound doesn’t have a plane of symmetry because it contains a chiral carbon.

Enantiomers are non-superimposable mirror images. Thus, the enantiomer of this compound is as follows:

The compound has two stereogenic centers. So, the diastereomers of the compound is as follows:

The compounds which have the chiral carbon atoms are as follows:

(d)

The structure of (1R,2R)-1,2-dibromocyclohexane is as follows:

If the carbon atom is attached to the four different groups or atoms, then that carbon is known as chiral carbon or chiral center. Here, the compound has two chiral centers and it is represented as follows:

Enantiomers are non-superimposable mirror images. Thus, the enantiomer of this compound is as follows:

The compound has two stereogenic centers. So, the diastereomers of the compound is as follows:

The compounds which have the chiral carbon atoms are as follows:

(e)

The structure of meso-hexane-3,4-diol is as follows:

If the carbon atom is attached to the four different groups or atoms, then that carbon is known as chiral carbon or chiral center. Here, the compound has two chiral centers and it is represented as follows:

Meso compounds have a plane of symmetry and forms two identical halves. So, the plane of symmetry of this compound is as follows:

Enantiomers are non-superimposable mirror images. This compound is given as meso compound. Thus, it does not exhibit the enantiomers.

The compound has two stereogenic centers. So, the diastereomers of the compound is as follows:

The compounds which have chiral carbon atoms are as follows:

(f)

The structure of -hexane-3,4-diol is as follows:

If the carbon atom is attached to the four different groups or atoms, then that carbon is known as chiral carbon or chiral center. Here, the compound has two chiral centers and it is represented as follows:

This compound doesn’t have a plane of symmetry because it contains a chiral carbon.

Enantiomers are non-superimposable mirror images. Thus, the enantiomers of this compound are as follows:

The compound has two stereogenic centers. So, the diastereomers of the compound is as follows:

The compounds which have chiral carbon atoms are as follows:

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