Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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A chemical compound that is represented with a molecular formula C6H12O6 is called L-(-) sugar. At the carbon’s 5th position, the hydroxyl group is placed to the compound’s left and therefore the sugar is represented as L(-)-sugar. It is capable of rotat…
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The image contains a series of chemical structures, each labeled as "The following intermediate." These intermediates appear to be part of a reaction sequence involving mercury acetate (Hg(OAc)₂) as a reagent. Here's a description of each: 1. **First Structure:** - Features a cyclic structure with an OH group and a positively charged mercury (Hg) bound to an acetate (OAc) group. - There's an OR group (possibly an alkoxide) and a CH₃ group attached. 2. **Second Structure:** - Another cyclic structure with an OAc group attached to a positively charged mercury (Hg). - It includes an OR group and a CH₃ group, with a hydrogen (H) also shown. 3. **Third Structure:** - A ring structure with a positively charged mercury (Hg) acetate complex. - OR and CH₃ groups are present, with a hydrogen (H). 4. **Fourth Structure:** - This shows a cyclic ether with mercury acetate (HgOAc) attached. - An OR group extends from the carbon adjacent to a CH₃ group. These structures likely represent intermediates in an organomercury reaction, possibly involving oxymercuration-demercuration or a similar transformation process. The arrows indicate movement of electrons or bonds, typical in reaction mechanisms.
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Transcribed Image Text:The image contains a series of chemical structures, each labeled as "The following intermediate." These intermediates appear to be part of a reaction sequence involving mercury acetate (Hg(OAc)₂) as a reagent. Here's a description of each: 1. **First Structure:** - Features a cyclic structure with an OH group and a positively charged mercury (Hg) bound to an acetate (OAc) group. - There's an OR group (possibly an alkoxide) and a CH₃ group attached. 2. **Second Structure:** - Another cyclic structure with an OAc group attached to a positively charged mercury (Hg). - It includes an OR group and a CH₃ group, with a hydrogen (H) also shown. 3. **Third Structure:** - A ring structure with a positively charged mercury (Hg) acetate complex. - OR and CH₃ groups are present, with a hydrogen (H). 4. **Fourth Structure:** - This shows a cyclic ether with mercury acetate (HgOAc) attached. - An OR group extends from the carbon adjacent to a CH₃ group. These structures likely represent intermediates in an organomercury reaction, possibly involving oxymercuration-demercuration or a similar transformation process. The arrows indicate movement of electrons or bonds, typical in reaction mechanisms.
**Reaction Mechanism and Intermediate Analysis** **Question:** Which of the following is a likely reaction intermediate/mechanism that best explains the following reaction? ©GMU 2020 **Chemical Reaction Steps:** 1. **Reactants:** - A cyclic alkene with a hydroxyl group (OH) and an alkoxy group (OR) attached. - A methyl (CH₃) group is also attached to the alkene. 2. **Reagents:** - Step 1: Hg(OAc)₂ - Step 2: NaBH₄ 3. **Product:** - A cyclic ether with an alkoxy group (OR) and an additional methyl group (CH₃) attached to the ring. **Proposed Intermediate:** - The mechanism proposes the formation of a mercurinium ion intermediate. - This intermediate includes a three-membered ring involving the mercury (Hg) atom, which is positively charged. - The hydroxyl (OH) group coordinates to the mercury atom, while an acetate ion (OAc) is displaced. - The molecular structure suggests a bridged cyclic ion, showing the stabilization of the positive charge through the formation of the mercurinium ion. This mechanism accounts for the regioselectivity and stereochemistry observed in the final cyclic ether product.
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Transcribed Image Text:**Reaction Mechanism and Intermediate Analysis** **Question:** Which of the following is a likely reaction intermediate/mechanism that best explains the following reaction? ©GMU 2020 **Chemical Reaction Steps:** 1. **Reactants:** - A cyclic alkene with a hydroxyl group (OH) and an alkoxy group (OR) attached. - A methyl (CH₃) group is also attached to the alkene. 2. **Reagents:** - Step 1: Hg(OAc)₂ - Step 2: NaBH₄ 3. **Product:** - A cyclic ether with an alkoxy group (OR) and an additional methyl group (CH₃) attached to the ring. **Proposed Intermediate:** - The mechanism proposes the formation of a mercurinium ion intermediate. - This intermediate includes a three-membered ring involving the mercury (Hg) atom, which is positively charged. - The hydroxyl (OH) group coordinates to the mercury atom, while an acetate ion (OAc) is displaced. - The molecular structure suggests a bridged cyclic ion, showing the stabilization of the positive charge through the formation of the mercurinium ion. This mechanism accounts for the regioselectivity and stereochemistry observed in the final cyclic ether product.
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