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converting 1-bromobutane

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damac:
Hi all i have a couple things i have to convert 1-bromobutane to

3. 1-butyne

does this look correct?

CH3CH2CH2CH2Br + NaC2CH --> CH3CH2C(triple bond)CH

4. CH3CH2CH2CH2CN
I think that i have found what was wrong with it

CH3CH2CH2Br + NaCN --> CH3CH2CH2CH2CN + NaBr

5. CH3CH2CH2CH2-O-C(=O)CH3

Not sure please help

akami:
1-Octane
You like heavy chemistry dude! simply make a Wurtz coupling (2 BuBr + Na gives C8H18 + NaBr)
The method you describe is ok for cross coupling

2-Butyne
SN reaction of your BuBr with water and alkali gives you BuOH. Dehydrate the alcohol on strong acid to obtain butene. Brominate your alkene to get 1,2-dibromobutane. React with alkali to obtain corresponding alkyne

3-valeronitrile
Simply react BuBr with alkaline cyanide like cyannure in an alcool

movies:
Another alternative for 1 would be direct reduction with LiAlD4 (lithium aluminum deuteride).

For octane (2), that reaction is called the Corey-House.  Should work fine for these purposes.

For 3, you could convert to the alkene directly by an E2 elimination with a very hindered base like sodium t-butoxide.  That would avoid having to make the alcohol.  The rest is as Akami wrote.

For 4, the only thing wrong is that you are missing a carbon in your butyl bromide starting material.  And you need a counterion for cyanide, say potassium.

For 5 I think you could get away with an SN2 displacement of Br with something like sodium acetate.  Alternatively, you could make the alcohol and then react the alcohol with acetic anhydride or acetyl chloride.  Lots of options.

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