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QUESTION

# How do you draw ( S )-1-bromo-1-chlorobutane?

Here's how I do it.

Step 1. Draw the structure of 1-bromo-1-chlorobutane.

Step 2. To get the stereochemical structure, start with the structure of butane.

Step 3. At "C-1", draw a wedge, a dash, and a solid bond.

Step 4. Put the "H" on the dashed bond. Then add the "Br" and "Cl" to the remaining bonds in any order.

We have a 50:50 chance of getting it right. Here's one possibility.

Step 5. Assign priorities to the groups.

"Br" = 1; "Cl" = 2; "C-2" = 3; "H" = 4.

Step 6. Assign stereochemistry

Then "Br" → "Cl" → "C-2" = 1 → 2 → 3 goes in a counterclockwise direction (S).

We got it right!

So this really is (S)-1-bromo-1-chlorobutane.

If we had gotten it wrong, we would have interchanged any two of the groups.

For example, in the diagram above, interchanging the "Cl" and "Br" atoms converts the (S) isomer to the (R) isomer.