Question

Converting from cyclohexene to this?

What reagents and conditions are required for this?

Answer 1

Well, you gots to make a `C-C` bond...

Explanation:

A tentative synthesis:

`(i)` `C_6H_10 + HBr rarr C_6H_11Br`

`(ii)` `C_6H_11Br+ Mg stackrel("dry ether")rarr C_6H_11MgBr`

`(iii)` `C_6H_11MgBr+ H(O=)C-CH_2CH_3 rarr` `C_6H_11-CH(OH)CH_2CH_3`

`(iv)` `C_6H_11-CH(OH)CH_2CH_3 stackrel(H_3PO_4, Delta)rarr`

`C_6H_10=CHCH_2CH_3`

Answer 2

How about this?

Explanation:

Step 1. Acid-catalyzed hydration of cyclohexene

Step 2. Wittig reaction

`bb((a))color(white)(m)underbrace(("C"_6"H"_5)_3"P")_color(red)("triphenylphosphine") + underbrace("Br-CH"_2"CH"_2"CH"_3)_color(red)("1-bromopropane") → underbrace(("C"_6"H"_5)_3stackrel("+")("P")"-CH"_2"CH"_2"CH"_3, "Br"^"-")_color(red)("triphenylpropylphosphonium bromide")`

`bb((b))color(white)(m)("C"_6"H"_5)_3stackrel("+")("P")"-CH"_2"CH"_2"CH"_3, "Br"^"-" + underbrace("CH"_3"CH"_2"CH"_2"CH"_2"-Li")_color(red)(n"-butyllithium") → underbrace(("C"_6"H"_5)_3"P=CHCH"_2"CH"_3)_color(red)("triphenylpropylidenephosphorane") + underbrace("CH"_3"CH"_2"CH"_2"CH"_3)_color(red)("butane") + "LiBr"`

Then