[etalas]

Hey, everyone! I'm stuck on this problem.
to
I've tried using KCN and then hydrolysis to turn it into a carboxylic acid but I then encounter a problem. I'm clueless on how to replace the carboxylic group with amide and keep the R group attached to the nitrogen. We are suppose to choose a reagent for that from a list but there is no amine, only ammonia, ammonium, and .
Not to mention after the second step that is partial hydrolysis, there is supposed to be a chain shortening according to the full problem. Any ideas?

[orgopete]

Have you studied N-alkylation reactions?

[discodermolide]

Try posting the full problem.

[etalas]

Have you studied N-alkylation reactions?

Not yet but if it is required, I imagine it would be taught in class later this week as the homework is due Friday.

Try posting the full problem.

I've attached it.

[discodermolide]

Why pick KCN from that list, that leads to an extra carbon. There are better reagents to choose from.
See if you can find them.