TBR ochem I p. 292 Units of Unsaturation

[zoner]

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How many units of unsaturation are present in the product of chlorocyclohexane and strong base and heat?

0
1
2
3

I said 1 but the answer is 2

My reasoning was that it was SN2 reaction due to a strong base. But the answer is suppose to be E2 mechanism thus two units of unsaturation.

Couldn't answer be both or rather more of SN2 duet to a strong base?

Thanks

 

[loveoforganic]

Cyclohexane's don't SN2 easily, despite secondary carbon status. Think of the sterics of getting behind the carbon. So it goes from a toss up of is it SN2/E2 with that strong base and secondary carbon to E2.