The correct option(s) of reagents and reaction sequences suitable for carrying out the following transformation is/are:
The correct option(s) of reagents and reaction sequences suitable for carrying out the following transformation is/are:
Show Hint
- (i) NBS, (PhCOO)2; (ii) aq. NaOH; (iii) active MnO2; (iv) Li/liq. NH3, t-BuOH
- (i) m-CPBA; (ii) BF3·Et2O
- (i) SeO2; (ii) Dess–Martin periodinane; (iii) K[BH(s-Bu)3] (K-selectride)
- (i) dil. KMnO4; (ii) NaIO4
The Correct Option is A, C
Solution and Explanation
The transformation is the conversion of cyclohexene to cyclohexanone. We must identify sequences that achieve this selectively.
- (A)
- (i) NBS, (PhCOO)2 → Allylic bromination of the double bond.
- (ii) aq. NaOH → Nucleophilic substitution to form allylic alcohol.
- (iii) MnO2 → Selective oxidation of allylic alcohol to enone.
- (iv) Li/NH3, t-BuOH → Birch reduction: 1,4-reduction of enone to ketone.
- This sequence is well-known for such transformations. CORRECT
- (B)
- (i) m-CPBA → Epoxidation of alkene.
- (ii) BF3·Et2O → Lewis acid mediated ring opening.
- This sequence does not lead efficiently to ketone. WRONG
- (C)
- (i) SeO2 → Allylic oxidation.
- (ii) Dess–Martin periodinane → Oxidation to enone.
- (iii) K-selectride → 1,4-reduction to ketone.
- This route is synthetically reliable. CORRECT
- (D)
- (i) dil. KMnO4 → Oxidative cleavage may occur.
- (ii) NaIO4 → Cleaves vicinal diols or enediols.
- These do not lead selectively to cyclohexanone. WRONG
\[ \boxed{\text{Correct options: (A), (C)}} \]
Top GATE CY Chemistry Questions
- Which among the following is true?
- The phosphazene compound that acts as a superbase is
- The reaction for the synthesis of Me2SiCl2 through the Rochow–Müller process is:
- Upon cooling from room temperature, the magnetic susceptibility of MnO slowly increases until 118 K, and then it decreases. This phenomenon is known as:
An aqueous solution of Co(ClO4)2·6H2O is light pink in colour. Addition of conc. HCl results in an intense blue coloured solution due to the formation of a new species. The new species among the following is:
[Given: Atomic number of Co = 27]
Top GATE CY Organic Reactions Questions
- The reaction for the synthesis of Me2SiCl2 through the Rochow–Müller process is:
For an unambiguous single step synthesis of the following target molecule (TM), the best bond disconnection in its retrosynthetic analysis is:
The correct option(s) of reagents and reaction sequences suitable for carrying out the following transformation is/are
Top GATE CY Questions
- Ψ(x) = \(\sqrt{\frac{32}{L^3}}\)[sin(\(\frac{\pi x}{L}\)).cos(\(\frac{\pi x}{L}\)).sin(\(\frac{2\pi y}{L}\)).sin(\(\frac{\pi z}{L}\))]Find the value of E221: E111.
what is the final product- Which are optically active?
intensity ratio of final product- Which among the following is true?