Confused on what the major product would be from this reaction sequence

Question

I'm struggling to figure out the steps and what the final major product would be.

https://imgur.com/a/uN43zoX

Answer 1

The final answer would be "D". You start out with an enamine which has the properties of an enolate nucleophile to accept the acetyl chloride electrophile. This has the net effect of an alpha acetylation. Following an aqueous acid work up, you restore the cyclopentanone and it has the beta-carbonyl (1,3-diketone). The next step is a sodium borohydride reduction of the 1,3-diketone and you end up with a 1,3-diol.

Answer 2

The nitrogen would push it's electrons down through the alkene so that the top right carbon on the ring would attack the nucleophilic carbonyl carbon, pushing electrons up onto the oxygen to form a tetrahedral intermediate. The oxygen would then push its electrons back down to reform the carbonyl and kick off the chlorine as a leaving group. The H3O+ would turn the imine into a ketone. Then in the next step the NaBH4 would reduce both ketones to alcohols, so the answer would be E. Hope that helps!