converting 1-bromobutane

[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

need help

[RobJim]

Sorry it's taken me so long to get back to you.

Hmm. Looks like you've removed 1. and 2.

3. 1-butyne

CH3CH2CH2CH2Br => {(CH3)3COH, (CH3)3COK} =>CH3CH2CH=CH2
CH3CH2CH=CH2 => {Br2} => CH3CH2CHBrCH2Br
CH3CH2CHBrCH2Br => {NaNH2, NH3} => CH3CH2C(bondx3)C(-)Na(+)
CH3CH2C(bondx3)C(-)Na(+) => {H2O} => CH3CH2C(bondx3)CH

I'm not sure what you mean by "NaC2CH".

4. CH3CH2CH2CH2CN

You got this one for the most part. My textbook also says to use DMSO as the solvent and to heat the reaction to 140-150 degrees C.

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

CH3CH2CH2CH2Br + CH3C(=O)OH

I think that should work.