What is the Fisher projection of #\text{(s)}-3-\text{bromo}-3-\text{chlorohexane}#?

1 Answer
May 7, 2018

Here's what I get.

Explanation:

The structure of 3−bromo−3−chlorohexane is

Structure

To get the 3D structure, I arbitrarily drew the wedge and dash as above (I had
a 50 % chance of getting it right).

If it turns out to be wrong, I will interchange #"Br"# and #"Cl"#.

To get the Fischer projection, we draw the carbon backbone vertically with #"C1"# at the top.

Fischer

Remember that the horizontal bonds must each be wedges.

We assign priorities as follows:

#"Br = 1, Cl = 2, C4 = 3, C2 = 4"#

Luckily, the lowest-priority group (#"C2"#) is behind the screen.

The #"1 → 2 → 3"# direction is counterclockwise, so this is the Fischer projection of (S)-3−bromo−3−chlorohexane.

Note: you could also use condensed structural formulas for the groups above and below #"C3"#, as in the structure below.

Condensed