Question

Match the reactions in List-I with the reagents in List-II:

List-I (Reactions) (A) 2-iodo-2-methylbutane $\rightarrow$ 2-methylbut-2-ene (B) tert-butyl alcohol $\rightarrow$ methyl tert-butyl ether (C) Cyclopentanol $\rightarrow$ Cyclopentanone (D) Cyclohex-2-en-1-ol $\rightarrow$ Cyclohex-2-en-1-one

List-II (Reagents) (I) (i) NaH, (ii) CH$_3$Br (II) K$^+$O$^-$C(CH$_3$)$_3$, (CH$_3$)$_3$COH (III) CrO$_3$Cl, CH$_2$Cl$_2$ (PCC in CH$_2$Cl$_2$) (IV) (i) TsCl, (ii) KI/acetone

• A. (A)-(II), (B)-(I), (C)-(III), (D)-(III)
• B. (A)-(I), (B)-(II), (C)-(IV), (D)-(III)
• C. (A)-(II), (B)-(III), (C)-(I), (D)-(IV)
• D. (A)-(IV), (B)-(I), (C)-(III), (D)-(II)

Answer 1

Answer: (A)

(A)-(II), (B)-(I), (C)-(III), (D)-(III)

Answer 2

• (A) $\rightarrow$ (II): 2-iodo-2-methylbutane undergoes E2 elimination with a strong, bulky base like potassium tert-butoxide (KOtBu) to form 2-methylbut-2-ene.
• (B) $\rightarrow$ (I): The formation of methyl tert-butyl ether from tert-butyl alcohol is a Williamson ether synthesis. NaH deprotonates the alcohol to form the alkoxide, which then reacts with CH$_3$Br.
• (C) $\rightarrow$ (III): Cyclopentanol (secondary alcohol) is oxidized to cyclopentanone using a mild oxidizing agent like Pyridinium Chlorochromate (PCC) in CH$_2$Cl$_2$.
• (D) $\rightarrow$ (III): Cyclohex-2-en-1-ol (secondary allylic alcohol) is oxidized to cyclohex-2-en-1-one using PCC in CH$_2$Cl$_2$.