QQuestionChemistry
QuestionChemistry
Identify what reagents you would use to achieve each transformation:
(a) Conversion of 2 -methyl- 2 -butene into a secondary alkyl halide
(b) Conversion of 2 -methyl- 2 -butene into a tertiary alkyl halide
(c) Conversion of cis- 2 -butene into a meso diol
(d) Conversion of cis- 2 -butene into enantiomeric diols
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Answer
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Step 1
2-methyl-2-butene + Br_2 \xrightarrow[heat~or~light]{} \text{secondary alkyl bromide}
To convert 2 -methyl- 2 -butene into a secondary alkyl halide, we can use a halogenation reaction with a halogen such as bromine (Br2) in the presence of light or heat. This will result in the addition of a bromine atom to the double bond, forming a secondary bromide.
Step 2
To convert 2 -methyl- 2 -butene into a tertiary alkyl halide, we can use a halogenation reaction followed by a reaction with a tertiary alcohol (such as tert-butanol) in the presence of sulfuric acid (H^2SO4) or phosphoric acid (H^3PO4). This two-step process is known as the Hunsdiecker reaction.
Final Answer
(a) 2 -methyl- 2 -butene + Br^2 (halogenation) (b) 2 -methyl- 2 -butene + Br^2 (halogenation) + tert-butanol + H^2SO^4 or H^3PO^4 (Hunsdiecker reaction) (c) cis- 2 -butene + HCOOH (epoxidation) + H^2O (hydrolysis) (d) cis- 2 -butene + H^2O^2 (asymmetric epoxidation) + H^2O (hydrolysis)
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