The NMR data giving for the product is as follows: d 7.05 (s, 5 H), 5.95–5.30 (m

Question

The NMR data giving for the product is as follows: d 7.05 (s, 5 H), 5.95–5.30 (m, 1 H), 5.19–4.80 (m, 2 H), 4.60 (t, J = 6 Hz, 1 H), 2.44 (t, J = 6 Hz, 2 H), 2.06 (br s, 1 H).

Part a) What proton is represented at "2.06 (br s, 1 H)"?

a) Proton connected to oxygen

b) Internal proton of the alkene

c) the proton that is on the carbon alpha to the alcohol

d) this is the impurity of water in DMSO

Part B) If you ran the NMR in d-DMSO and see an additional peak at 1.76ppm and 3.60ppm, what do these peaks represent.

a) redidue THF impurity, as THF was used as a solvent in the reaction

b) allyl bromide starting material

c) benzaldehyde starting material

d) water impurity as water was used as a solvent in the reaction

e) these resonances represent the protons of ammonium chloride which was used in the reaction

Explanation / Answer

Part a) What proton is represented at "2.06 (br s, 1 H)"?

c) the proton that is on the carbon alpha to the alcohol

Broad singlet always will appear when OH and NH2 present in the compound.

Part B) If you ran the NMR in d-DMSO and see an additional peak at 1.76ppm and 3.60ppm, what do these peaks represent.

a) redidue THF impurity, as THF was used as a solvent in the reaction

THF will show 2 triplet peaks in proton NMR.

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