JEE PYQ: Hydrocarbons Question 26
Question 26 - 2020 (07 Jan Shift 1)
Consider the following reactions:
(a) $(\text{CH}_3)_2\text{CCH}(\text{OH})\text{CH}_3 \xrightarrow{\text{conc. H}_2\text{SO}_4}$ (b) $(\text{CH}_3)_2\text{CHCH}(\text{Br})\text{CH}_3 \xrightarrow{\text{alc. KOH}}$ (c) $(\text{CH}_3)_2\text{CHCH}(\text{Br})\text{CH}_3 \xrightarrow{(\text{CH}_3)_3\text{CO}^-\text{K}^+}$ (d) $(\text{CH}_3)_2\text{C}(-\text{OH})-\text{CH}_2-\text{CHO} \xrightarrow{\Delta}$
Which of these reaction(s) will not produce Saytzeff product?
(1) (a), (c) and (d)
(2) (d) only
(3) (c) only
(4) (b) and (d)
Show Answer
Answer: (3)
Solution
(A) Conc. $\text{H}_2\text{SO}_4$ gives Saytzeff product. (B) Alc. KOH gives Saytzeff product. (C) Due to bulky nature of tertiary butoxide, the least hindered hydrogen is eliminated. Therefore, Hoffman product is formed. (D) $(\text{CH}_3)_2\text{C}(-\text{OH})-\text{CH}_2-\text{CHO} \xrightarrow{\Delta}$ gives Saytzeff product.
BETA
