How can I draw all possible stereoisomers for 2-bromo-4-chlorohexane?

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Answer 1 · 2015-08-27T16:09:21

Identify the chiral centres and then draw all the possibilities.

Step 1. Draw the bond-line structure for 2-bromo-4-chlorohexane.

Bond-Line

Step 2. Identify the chiral centres.

The chiral centres are $"C-2"$ and $"C-4"$ .

Step 3. Calculate the number of possible stereoisomers.

The maximum number of stereoisomers is $2^n$ , where $n$ is the number of chiral centres.

Here, $n=2$ . and $2^2 =4$ , so there are four possible stereoisomers.

Step 4. Draw the stereoisomers.

If we indicate the stereochemistry of the bonds to the heteroatoms by wedges and dashes, the structures are

Wedge-Wedge

Wedge-Dash

Dash-Wedge

Dash-Dash

Step 5. Check for meso isomers.

There is no internal plane of symmetry, so there are no meso isomers.

The above structures are all unique stereoisomers.