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A student exposed r-1-bromo-2-propanol to sodium hydroxide, isolated an optically active product, and collected the proton nmr below. what is the structure of the compound that the student isolated?

User Taya
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The structure of the compound that the student isolated is 2-methylpropan-1-ol. This compound is optically active because it has a chiral center.

The proton NMR spectrum of the isolated product shows different signals. A singlet at 1.1 ppm due to the presence of three equivalent methyl group. A singlet at 4.2 ppm due to the presence of a methylene group (-CH2-)

Note that R-1-bromo-2-propanol is a primary alkyl halide, which means that it will undergo a SN2 reaction with sodium hydroxide. In an SN2 reaction, the nucleophile (OH-) attacks the back side of the carbon atom bearing the leaving group (Br-) and displaces it.

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3. A student exposed R-1-bromo-2-propanol to sodium hydroxide, isolated an optically active product, and collected the proton NMR below. What is the structure of the compound that the student isolated?

A student exposed r-1-bromo-2-propanol to sodium hydroxide, isolated an optically-example-1
User Maddy D
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