1.

What product is expected when tertiary butyl bromide is reacted with sodium ethoxide? Why that product is not formed and how that product can be obtained?

Answer»

Solution :`CH_3-underset(CH_3)underset(|)overset(CH_3)overset(|)(C )-Br+NaOC_2H_5underset(-NaBr)(rarr)CH_3-underset(CH_3)underset(|)overset(CH_3)overset(|)(C )-OC_2H_5`
The EXPECTED product is shown above. But the MAJOR product is 2-methyl-1-propene. This is because sodium ethoxide is a STRONG nucleophile as WELL as a strong buse. Thus elimination REACTION predominates over substitution. The product in the reaction can be obtained as
`CH_3-underset(CH_3)underset(|)overset(CH_3)overset(|)(C )-Br+NaOC_2H_5underset(-NaBr)(rarr)CH_3-underset(CH_3)underset(|)overset(CH_3)overset(|)(C )-OC_2H_5`


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