What is the major organic product obtained from the following sequence of reactions?
E) 6,6-dimethyl-1-hexene
E) 5,5-dimethyl-1-heptene
E) 6,6-dimethyl-1-heptene
E) 6,6-dimethyl-2-heptene

Question

What is the major organic product obtained from the following sequence of reactions? 
E) 6,6-dimethyl-1-hexene 
E) 5,5-dimethyl-1-heptene 
E) 6,6-dimethyl-1-heptene 
E) 6,6-dimethyl-2-heptene

Quizplus · Accepted Answer

The starting material is an alkene with a double bond between carbons 2 and 3. After reaction with HBr, the double bond breaks and a Br atom is added to each carbon, resulting in a 1,2-dibromoalkane. Treatment with sodium methoxide (NaOMe) results in elimination of HBr and the formation of the corresponding alkene with two methyl groups on the same carbon. The two methyl groups will be trans (on opposite sides of the double bond) due to the mechanism of the elimination reaction. The final product is (E) 6,6-dimethyl-2-heptene, since the starting material has seven carbons and the product must have the same number of carbons.

What Is the Major Organic Product Obtained from the Following