[frankenstein18]

Can someone tell me if I'm on the right track with these intramolecular reactions?

For a) I think that an epoxide is formed after NaH takes a Hydrogen from the OH substituent and then the electrons travel making the Cl leave.

Then for b I know an epoxide can't form since the OH and the Cl are on the same side. I think the NaH would take the H, so would the product be a resonance structure???

For c. I think it's a 5 carbon hetero-cyclic ring with an Oxygen closing the ring + NaH2 and Br-

And for d. I think another hetero cyclic ring happens but I don't know what it would look like.I don't know it's substituents or how long it would be since it's not a long chain like how c was.

Am I in the right direction?

[beardy]

a. yeah

b. (source: http://www.masterorganicchemistry.com/2015/01/26/epoxides-the-outlier-of-the-ether-family/)

c. yeah

d. looks like sn2 epoxide formation. hydroxyl gets deprotonated from sodium hydride, attacks alkyl halide through backside attack. this is a straight chain tho with no stereochemistry so i cant completely confirm here