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n each case below select the synthetic procedure that could be used to carry out the transformation shown. The procedures are: Epoxidation/hydrolysis: alkene + meta-chloroperoxybenzoic acid; then H3O*. OsO4 oxidation: alkene + OsO4; then NaHSO3 CH₂OH НО CH3CH=C(CH3)2 CH₂OH HO OH CH3CHC(CH3)2 neither method Os04 oxidation

n each case below select the synthetic procedure that could be used to carry out the transformation shown. The procedures are: Epoxidation/hydrolysis: alkene + meta-chloroperoxybenzoic acid; then H3O*. OsO4 oxidation: alkene + OsO4; then NaHSO3 CH₂OH НО CH3CH=C(CH3)2 CH₂OH HO OH CH3CHC(CH3)2 neither method Os04 oxidation

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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### Synthetic Procedures for Alkene Transformations In each case below select the synthetic procedure that could be used to carry out the transformation shown. **The procedures are:** 1. **Epoxidation/hydrolysis**: alkene + *meta*-chloroperoxybenzoic acid; then H₃O⁺. 2. **OsO₄ oxidation**: alkene + OsO₄; then NaHSO₃. #### Transformations: 1. **First Transformation** - **Starting Material**: - Cyclopentene with a hydroxymethyl group (—CH₂OH) on the 1st position. - **Product**: - Cyclopentane with two hydroxyl groups (—OH), one where the double bond was and one on the 1st position, leaving the hydroxymethyl group (—CH₂OH) intact. - **Correct Synthetic Procedure**: - Neither method - **Reasoning**: - Neither epoxidation/hydrolysis nor OsO₄ oxidation will specifically produce the shown product. The transformation shown cannot be achieved with the given synthetic procedures. 2. **Second Transformation** - **Starting Material**: - 2,3-dimethyl-2-butene (CH₃CH═C(CH₃)₂) - **Product**: - 2,3-dimethyl-2,3-butanediol (CH₃CH(COH)(OH)C(CH₃)₂) - **Correct Synthetic Procedure**: - OsO₄ oxidation - **Explanation**: - OsO₄ oxidation is suitable for syn-dihydroxylation of the alkene, adding two hydroxyl groups to the same side of the double bond. This selection process involves understanding the reactions by which these synthetic procedures transform alkenes into specific products.
Transcribed Image Text:### Synthetic Procedures for Alkene Transformations In each case below select the synthetic procedure that could be used to carry out the transformation shown. **The procedures are:** 1. **Epoxidation/hydrolysis**: alkene + *meta*-chloroperoxybenzoic acid; then H₃O⁺. 2. **OsO₄ oxidation**: alkene + OsO₄; then NaHSO₃. #### Transformations: 1. **First Transformation** - **Starting Material**: - Cyclopentene with a hydroxymethyl group (—CH₂OH) on the 1st position. - **Product**: - Cyclopentane with two hydroxyl groups (—OH), one where the double bond was and one on the 1st position, leaving the hydroxymethyl group (—CH₂OH) intact. - **Correct Synthetic Procedure**: - Neither method - **Reasoning**: - Neither epoxidation/hydrolysis nor OsO₄ oxidation will specifically produce the shown product. The transformation shown cannot be achieved with the given synthetic procedures. 2. **Second Transformation** - **Starting Material**: - 2,3-dimethyl-2-butene (CH₃CH═C(CH₃)₂) - **Product**: - 2,3-dimethyl-2,3-butanediol (CH₃CH(COH)(OH)C(CH₃)₂) - **Correct Synthetic Procedure**: - OsO₄ oxidation - **Explanation**: - OsO₄ oxidation is suitable for syn-dihydroxylation of the alkene, adding two hydroxyl groups to the same side of the double bond. This selection process involves understanding the reactions by which these synthetic procedures transform alkenes into specific products.
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