How would we perform the following chemical transformations?

Question

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

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Answer 1 · 2017-01-19T17:48:31

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

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.