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Elimination reactions of vicinal dibromide
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Leopoldo Mauro Collaoni
Elimination reactions of vicinal dibromide
After the first elimination, you have a vinylic bromide, so there are two options for the second elimination. The two acidic hydrogens that the base can abstract are one attached to sp2 carbon and one to sp3. Since sp2 hybridized carbon is more electronegative, the base abstracts the hydrogen attached to it, and then bromine leaves being a good leaving group, which gives alkyne as the major product.
After the first elimination, you have a vinylic bromide, so there are two options for the second elimination. The two acidic hydrogens that the base can abstract are one attached to sp2 carbon and one to sp3. Since sp2 hybridized carbon is more electronegative, the base abstracts the hydrogen attached to it, and then bromine leaves being a good leaving group, which gives alkyne as the major product.
After the first elimination, you have a vinylic bromide, so there are two options for the second elimination. The two acidic hydrogens that the base can abstract are one attached to sp2 carbon and one to sp3. Since sp2 hybridized carbon is more electronegative, the base abstracts the hydrogen attached to it, and then bromine leaves being a good leaving group, which gives alkyne as the major product.
After the first elimination, you have a vinylic bromide, so there are two options for the second elimination. The two acidic hydrogens that the base can abstract are one attached to sp2 carbon and one to sp3. Since sp2 hybridized carbon is more electronegative, the base abstracts the hydrogen attached to it, and then bromine leaves being a good leaving group, which gives alkyne as the major product.
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