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in Some basic principles of organic chemistry by (145 points)
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One mole of d-2-bromobutane is hydrolyzed in an alkaline medium to form butane-2-ol. The rate of formation of l-butane-2-ol is assumed to be twice that of d-butane-2-ol. The specific rotation of d-butane-2-ol is +13.5°. After complete reaction, the specific rotation of the product mixture is:

(1) -4.5°

(2) +4.5°

(3) -5.5°

(4) +13.5°

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∵ the rate of formation of l-butane-2-ol is twice the rate of formation of d-butane-2-ol.

∴ On hydrolysis of d-2-bromobutane field 66.6% l-butane-2-ol and 33.3% d-butane-2-ol.

∴ enantiomeric excess = 66.6% - 33.3%

ee% = 33.3%

∵ We have given, Specific rotation of pure d-butane-2-ol is +13.5° is specific rotation of pure l-butane-2-ol is -13.5°

as we know

ee% = \(\frac{|\text{Oberserved} \,\alpha|}{|\alpha \,\text{of pure enantiomer of excessisomer}|}\times100\)%

⇒ observed specific rotation = \(\frac{33.3 \times(-13.5)^\circ}{100}\)

= -4.495° or -4.5°

Hence, specific rotation of the product mixture will be -4.5°.

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