The Student Room Group
Competition - post a photo you've taken of nature >>
Competition - post a photo you've taken of nature >>
Competition - post a photo you've taken of nature >>

Converting and Alkene into other things help

Haven't done this since AS and need some help.

I have to convert Propene into:

a.) CH3CH(OH)CH3 - Add HCl followed by NaOH
b.) CH3COCH3 - Heat part a under eflux with dilute sulfuric acid and potassium dichromate VI
c.) CH3C(OH)(CN)CH3 - add KCN and HCN to part b at pH 8
d.) (CH3)2CHCN - ??? All I need to do here is replace the hydroxyl group in part C with a Hydrogen and forgot how to do that
e.) (CH3)2CHCH2NH2 - Part d + LiAlH4 in dry ether and then hydrolyse with sulfuric acid
f.) CH3CH(OH)CH2OH - Really stumped by this one :confused:

Any help on part d and f will be appreciated.
Reply 1
Avatar for shengoc
shengoc
12
Original post by chaz1992
Haven't done this since AS and need some help.

I have to convert Propene into:

a.) CH3CH(OH)CH3 - Add HCl followed by NaOH
b.) CH3COCH3 - Heat part a under eflux with dilute sulfuric acid and potassium dichromate VI
c.) CH3C(OH)(CN)CH3 - add KCN and HCN to part b at pH 8
d.) (CH3)2CHCN - ??? All I need to do here is replace the hydroxyl group in part C with a Hydrogen and forgot how to do that
e.) (CH3)2CHCH2NH2 - Part d + LiAlH4 in dry ether and then hydrolyse with sulfuric acid
f.) CH3CH(OH)CH2OH - Really stumped by this one :confused:

Any help on part d and f will be appreciated.


(f) this is a dihydroxylation. You can use,
http://www.organic-chemistry.org/synthesis/C1O/diols2.shtm

(d) is simpler than you thought. add HCN across alkene, simple markovnikov rule puts H on the terminal alkene leaving you secondary carbocation and CN- adds in.
Going from (c) to (d) is hard because cyanohydrin(species in c) is reversible with the keto form in acid, so not really a good starting point.
(edited 13 years ago)

Quick Reply

Related discussions

Latest

Trending

Trending

Articles for you