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11. When (S)-2-bromo-3-methylbutane (3) is treated with sodium hydroxide, a mixture of two products (4 and 5) results. OH CH3 H3C CH3 CH3 CH3 Assign one of the three IR spectra below to each compound and identify peaks within each spectrum that allowed you to make these assignments.

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Answer #1

The 1st IR spectra is for product 5. Product 5 has alkene C-H stretching which is around 3050 cm-1 which is present in 1st IR spectra. 2nd IR spectra is for product 4. The presence of OH group has a broad IR O-H stretching present around 3400cm-1 which is present only in 2nd spectra. And the 3rd IR spectra is for reactant 3. It has only sp3 C-H stretching around 2900cm-1.

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