Problem: Compounds A and B are isomers of molecular formula C9H19Br. Both yield the same alkene C as the exclusive product of elimination on being treated with potassium  tert -butoxide in dimethyl sulfoxide. Hydrogenation of alkene C gives 2,3,3,4-tetramethylpentane. What are the structures of compounds A and B and alkene C?      

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Compounds A and B are isomers of molecular formula C9H19Br. Both yield the same alkene C as the exclusive product of elimination on being treated with potassium  tert -butoxide in dimethyl sulfoxide. Hydrogenation of alkene C gives 2,3,3,4-tetramethylpentane. What are the structures of compounds A and B and alkene C?    
 

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Carey 8th Edition. You can also practice Organic Chemistry - Carey 8th Edition practice problems.