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The correct match between Column I and Column II is :

Column IColumn II
(i) p-xylene(a) one signal in 1H-NMR and two signals in 13C-NMR
(ii) 4-methyl cyclohexanone(b) 2210 cm−1 in IR
(iii) 1-Butyne(c) Two singlets in 1H-NMR
(iv) 2, 2-dimethyl propane(d) λmax 280 (∈ 30) in UV

  • A.(i-a) (ii-b) (iii-c) (iv-d)
  • B.(i-c) (ii-d) (iii-b) (iv-a)
  • C.(i-a) (ii-b) (iii-d) (iv-c)
  • D.(i-c) (ii-b) (iii-d) (iv-a)

Answer: B

The correct match is (i-c) (ii-d) (iii-b) (iv-a).

  1. p-Xylene shows two singlets in 1H-NMR, the four ring H and the six methyl H (c).
  2. 4-Methylcyclohexanone, a saturated ketone, has the weak n→π* band near 280 nm with ε about 30 (d).
  3. 1-Butyne has a C≡C stretch in the IR, which the key places at 2210 cm−1 (b).
  4. 2,2-Dimethylpropane has twelve equivalent H, one 1H signal, and two kinds of carbon, two 13C signals (a).

Option A gives p-xylene a single proton signal, which ignores the aromatic H, and options C and D give the UV band of a ketone to an alkyne.

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