Question

Label the boxed functional groups in the steroid molecule.

1)

Label the boxed functional groups in the steroid molecule. In each reaction box, place the best reagent and conditions from the list below. In each reaction box, place the best reagent and conditions from the list below.

2)

3)

Answer 1

Question 1

Functional groups need to be memorized sadly. I have listed them in the image below.

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Question 2

The reaction scheme is shown below. First alkylate the alkyne by deprotonating with NaNH₂. This forms a carbon nucleophile which can attack CH₃CH₂Br. The alkyne can then react with one equivalent with Br₂ in order to retain the alkene.

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Question 3

This synthesis is relatively straightfoward. Reduce the aldehyde with sodium borohydride to the alcohol. The alcohol can be converted into a good leaving group (Br) with PBr₃. Finally, adding NaCN will give the corresponding nitrile through SN2 substitution.