[sirpaul]

I have to make N-ethyl-N-isopropyl pentanamide starting with hydrocarbons. Any hints on how to do it?

[sjb]

What functional group(s) are there present in your target molecule?

[sirpaul]

The compound is an amide, that has an ethyl and isopropyl group attached to the nitrogen. What I did is create 2-bromopropane through the hydrohalogenation reaction. I then reacted the 2-bromopropane with N-pentanamide to create N-isopropyl pentanamide. I would then repeat the process with the ethyl part. I don't think this is correct. My way of thinking was that the reaction would kick out the Br and bond to the N.

[sjb]

The compound is an amide, that has an ethyl and isopropyl group attached to the nitrogen. What I did is create 2-bromopropane through the hydrohalogenation reaction. I then reacted the 2-bromopropane with N-pentanamide to create N-isopropyl pentanamide. I would then repeat the process with the ethyl part. I don't think this is correct. My way of thinking was that the reaction would kick out the Br and bond to the N.

This would work, nothing wrong there. How would you make pentanamide, though?

[sirpaul]

I put 1-pentanol through a hydration reaction, resulting in pentanol. I then oxydized pentanol, then pentanal to give pentanoic acid. By reacting pentanoic acid with ammonia (substitution reaction?) I got the pentamide. I then just added 2-bromopropane and 1-bromoethane to the pentamide (one by one of course) to get my final molecule. Is this correct? And are those just called addition reactions?

[sjb]

It's not wrong, but whether there are other, better ways is left as an exercise in retrosynthesis