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Compound A, an alkyl bromide with chemical formula , reacts with to yield compou

ID: 853509 • Letter: C

Question

Compound A, an alkyl bromide with chemical formula , reacts with to yield compound B. Compound B in turn reacts with (1) , (2) , to yield compound C. Compound C reacts with to yield compound D. Propose a structure for compound B that is consistent with the following predicted 1H-NMR spectrum.

Compound A, an alkyl bromide with chemical formula , reacts with to yield compound B. Compound B in turn reacts with (1) , (2) , to yield compound C. Compound C reacts with to yield compound D. Propose a structure for compound B that is consistent with the following predicted 1H-NMR spectrum. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.

Explanation / Answer

Potassium tert-butoxide will result in an elimination reaction with an alkyl halide, thus, Compound B will be propene. Alkenes show signals in the 5-6 ppm range in proton NMR.

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