Question

Which structure is consistent with the following proton NMR data: 1.2 (3H, triplet, J = 8Hz), 3.7 (2H, quartet, J = 8Hz), 4.1 (2H, singlet) 11.1 (1H, singlet) CH,CH3 OCH, or OOOO co

Answer 1

Correct option: C

Peak assignment:

1.2 (3H, triplet, J = 8Hz) ОН - 11.1 (1H, singlet) 3.7 (2H, quartet, J = 8Hz) 4.1 (2H, singlet)

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Correct option: C

1. NaOEt 2. PhCH Br ihn s iin om in H30 , heat Ph Ph

Step 1:

Ethoxide abstracts one of the active methylene hydrogen to generate a carbanion. The carbanion thus formed the attacks the benzyl bromide in S_N2 fashion to give the intermediate.

Step 2:

Aqueous acidic hydrolysis of ester followed by decarboxylation of the beta-keto acid gives the product.