[untitled]

Hi,

There are 3 synthesis reactions that I'm stuck with. What's in black is the question
(reaction-->product) and what's in red is what I've tried doing. Can anyone help me with them to know what's right and what's wrong? Thank you!

[AWK]

Reaction 1 is reliable, though there is a printing error, and something more is needed
Raction 2 is unreliable.
The last step of reaction 3 is wrong

[Albert]

What about using NaH in the second reaction?

[untitled]

How would NaH lead to the product? You still need something no?

[AWK]

Reaction 1 produces CH2=C6H10. You should isomerize this compound to 1-methyl-1-cyclohexene (by thermal or chemical way)
In reaction 2 , NaOH cause elimination, in this case rather to CH2=C5H8. Anti-Markovnikow addition of BH3 and oxidation can produce needed alcohol
In reaction 3, step 2, elimination of HBr produces CH2=C5H8, then oxidation of double bond gives diol

[Albert]

In reaction 3, step 2, elimination of HBr produces CH2=C5H8, then oxidation of double bond gives diol

Yes, exactly. I'd carry out the former with (CH3)3COK and (CH3)3COH (according to Hofmann's Rule) and the latter using KMnO4 (0°C, pH = 7) or OsO4 (if you like expensive things  ).