Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Question
**Chemical Reaction Reagents and Transformations** **Instructions:** Select from the available reagents the one you would use to carry out each of the transformations below. **Reagents Available:** - a. KOH - b. KMnO₄, H₃O⁺ - c. H₂, Pd - d. CH₂I₂, Zn(Cu) - e. Hg(OAc)₂, H₂O; then NaBH₄ - f. OsO₄; then NaHSO₃ - g. BH₃; then H₂O₂, ⁻OH - h. CHCl₃, KOH - i. O₃; then Zn, H₃O⁺ - j. H₂SO₄ - k. Cl₂ - l. Cl, CO₃H, then H₃O⁺ **Transformations and Reagents Selection:** 1. **Transformation 1:** - **From:** Cyclopentene - **To:** Cis-1,2-cyclopentanediol - **Reagent to Use:** f. OsO₄; then NaHSO₃ - **Explanation:** Osmium tetroxide (OsO₄) followed by sodium bisulfite (NaHSO₃) is commonly used for dihydroxylation, converting an alkene to a vicinal diol with syn-stereochemistry. 2. **Transformation 2:** - **From:** 1-Methylcyclopentene - **To:** 2-Methylcyclopentanol - **Reagent to Use:** g. BH₃; then H₂O₂, ⁻OH - **Explanation:** Hydroboration-oxidation (BH₃ followed by H₂O₂ and hydroxide) leads to anti-Markovnikov hydration of alkenes, forming alcohols at the least substituted carbon of the double bond.
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Transcribed Image Text:**Chemical Reaction Reagents and Transformations** **Instructions:** Select from the available reagents the one you would use to carry out each of the transformations below. **Reagents Available:** - a. KOH - b. KMnO₄, H₃O⁺ - c. H₂, Pd - d. CH₂I₂, Zn(Cu) - e. Hg(OAc)₂, H₂O; then NaBH₄ - f. OsO₄; then NaHSO₃ - g. BH₃; then H₂O₂, ⁻OH - h. CHCl₃, KOH - i. O₃; then Zn, H₃O⁺ - j. H₂SO₄ - k. Cl₂ - l. Cl, CO₃H, then H₃O⁺ **Transformations and Reagents Selection:** 1. **Transformation 1:** - **From:** Cyclopentene - **To:** Cis-1,2-cyclopentanediol - **Reagent to Use:** f. OsO₄; then NaHSO₃ - **Explanation:** Osmium tetroxide (OsO₄) followed by sodium bisulfite (NaHSO₃) is commonly used for dihydroxylation, converting an alkene to a vicinal diol with syn-stereochemistry. 2. **Transformation 2:** - **From:** 1-Methylcyclopentene - **To:** 2-Methylcyclopentanol - **Reagent to Use:** g. BH₃; then H₂O₂, ⁻OH - **Explanation:** Hydroboration-oxidation (BH₃ followed by H₂O₂ and hydroxide) leads to anti-Markovnikov hydration of alkenes, forming alcohols at the least substituted carbon of the double bond.
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