How would we perform the following chemical transformations?

"1. ethyl bromide to 2-butanol;"
"2. ethyl bromide to ethyl alcohol;"
"3. ethyl bromide to ethane;"
"4. ethyl bromide to ethyl chloride?"
"5. ethyl bromide to acetic acid;"
"6. ethyl bromide to ethylene;"
"7. ethyl bromide to propane?"

1 Answer
Jan 19, 2017

To make C-C bonds, the obvious strategy is to make Grignard reagents.........

Explanation:

These are possible reactions; there are many alternatives, and the proposed route might be highly impractical:

1. "ethyl bromide "rarr" n-butane":

C_2H_5Br + Mg rarr C_2H_5MgBr;

C_2H_5MgBr + H(O=C)CH_3rarrH_3C-CH_2CH(OH)CH_3

(the alcohol results after aqueous workup of the magnesium alkoxide.)

H_3C-CH_2CH(OH)CH_3 +Delta + H_3PO_4rarr"butylene + water"

"butylene"+H_2(g) rarr "n-butane"

2. "ethyl bromide "rarr" ethyl alcohol":

C_2H_5Br + "KOH/NaOH" rarr C_2H_5OH + "KBr/NaBr"

3. "ethyl bromide "rarr" ethane":

C_2H_5Br + "KOH/NaOH" rarr C_2H_5OH + "KBr/NaBr"

C_2H_5OH + H_3PO_4 rarr H_2C=CH_2 + H_2O

H_2C=CH_2 + H_2" (+metal catalyst)" rarr H_3C-CH_3;

4. "ethyl bromide "rarr" ethyl chloride":

C_2H_5Br + KOBu^t rarr H_2C=CH_2 + KBr + Bu^tOH

H_2C=CH_2 + H-Cl rarr H_3C-CH_2Cl;

5. "ethyl bromide "rarr" acetic acid":

C_2H_5Br + KOH rarr H_3C-CH_2OH + KBr;

H_3C-CH_2OH + KMnO_4 rarr H_3C-CO_2H + MnO_2

6. "ethyl bromide "rarr" ethylene":

C_2H_5Br + KOBu^t rarr H_2C=CH_2 + KBr + Bu^tOH

7. "ethyl bromide "rarr" propane":

C_2H_5Br + Mg rarr C_2H_5MgBr;

C_2H_5MgBr + O=C(OC_2H_5)_2 rarr H_3C-CH_2C(=O)OCH_2CH_3

H_3C-CH_2C(=O)OCH_2CH_3 + LiAlH_4rarr
H_3C-CH_2CH_3
This reduction reaction would be hard to accomplish.

Again, these are suggestions. There are many possibilities.