Question

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?"`

Answer 1

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.