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Compound X has molecular formula C7H14. Hydrogenation of
Chapter 9, Problem 9.75(choose chapter or problem)
Compound X has molecular formula C7H14. Hydrogenation of compound X produces 2,4- dimethylpentane. Hydroboration-oxidation of compound X produces a racemic mixture of 2,4- dimethyl-1-pentanol (shown below). Predict the major product(s) obtained when compound X is treated with aqueous acid (H3O+). 2,4-Dimethyl-1-pentanol OH
Questions & Answers
QUESTION:
Compound X has molecular formula C7H14. Hydrogenation of compound X produces 2,4- dimethylpentane. Hydroboration-oxidation of compound X produces a racemic mixture of 2,4- dimethyl-1-pentanol (shown below). Predict the major product(s) obtained when compound X is treated with aqueous acid (H3O+). 2,4-Dimethyl-1-pentanol OH
ANSWER:Step 1 of 2
The key to determining Compound X’s structure is by examining the hydroboration- oxidation product. This reaction gives the anti-Markovnikov product, so the alkene reactant must be between the carbon that is now attached to the hydroxyl and the adjacent carbon. This gives the structure of Compound X.