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Consider compound A (2-bromo-4-tert-butyl-1-methylcyclohexane), below. When an u

ID: 911515 • Letter: C

Question

Consider compound A (2-bromo-4-tert-butyl-1-methylcyclohexane), below. When an unknown stereoisomer of A is treated with potassium tert-butoxide, the only alkene product formed is one of the possible stereoisomers of 1-tert-butyl-4-methylcylohex-2-ene (compound B). In box 4A. Draw the chair conformer of the stereoisomer of compound A that would match this observation, and explain why only one alkene product is possible upon elimination. Stereoisomers of tartaric acid can be prepared from one of two butenedioic acids, fumaric acif or maleic acid. In box 5A, identify which of these two acids could be used to prepare mesotataric acid by syn-dihydroxylation. Use Newman projections to support your reasoning.

Explanation / Answer

Syn hydroxylation of maleic acid gives meso tartaric acid