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OTMS OTMS OH "MgBr /Br OH OTMS ICH,OH CH2OH B- TMS-CI/pyridine C- MgBr2/ether A- TMS-OH/pydidine E- H3O* F-1. (CH3)2C=O 2. H3O* D- Mg/THF G- 1. H2С%-D0 2. НзО*

OTMS OTMS OH "MgBr /Br OH OTMS ICH,OH CH2OH B- TMS-CI/pyridine C- MgBr2/ether A- TMS-OH/pydidine E- H3O* F-1. (CH3)2C=O 2. H3O* D- Mg/THF G- 1. H2С%-D0 2. НзО*

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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Identify the correct reagents with the correct letter for carrying out the following synthesis.

The diagram illustrates a multistep organic synthesis pathway starting from a bromocyclohexanol compound. 1. **Step 1**: The initial compound is cyclohexanol with a bromine atom (Br) attached. This reacts to form a silyl ether where the hydroxyl group (OH) is protected with a trimethylsilyl (TMS) group. 2. **Reagent A (TMS-OH/pyridine)**: This reagent is used for the TMS protection of the hydroxyl group. 3. **Step 2**: The TMS-protected bromocyclohexane then undergoes a Grignard reaction where the bromine is replaced with a magnesium bromide group (MgBr). 4. **Reagent C (MgBr2/ether)**: This facilitates the formation of the Grignard reagent. 5. **Step 3**: The Grignard reagent is then treated with formaldehyde (H₂C=O), leading to the formation of an alcohol with an additional methylene group. 6. **Reagent G (1. H₂C=O 2. H₃O⁺)**: The addition of formaldehyde followed by acid work-up (H₃O⁺) results in the alcohol product. 7. **Step 4**: Finally, the TMS protecting group is removed, yielding the final product, an alcohol with a newly introduced hydroxymethyl group at the position where the Grignard reaction took place. The other reagents mentioned in the diagram include: - **Reagent B (TMS-Cl/pyridine)**: This is another method of introducing the TMS protecting group, using TMS chloride instead of TMS-OH. - **Reagent D (Mg/THF)**: Typically used for preparing Grignard reagents. - **Reagent E (H₃O⁺)**: Acidic work-up used to quench reactions. - **Reagent F (1. (CH₃)₂C=O 2. H₃O⁺)**: Alternate addition of acetone, followed by acid work-up, which can introduce additional structural changes. This sequence demonstrates functional group transformations using protection and conversion strategies in organic synthesis.
Transcribed Image Text:The diagram illustrates a multistep organic synthesis pathway starting from a bromocyclohexanol compound. 1. **Step 1**: The initial compound is cyclohexanol with a bromine atom (Br) attached. This reacts to form a silyl ether where the hydroxyl group (OH) is protected with a trimethylsilyl (TMS) group. 2. **Reagent A (TMS-OH/pyridine)**: This reagent is used for the TMS protection of the hydroxyl group. 3. **Step 2**: The TMS-protected bromocyclohexane then undergoes a Grignard reaction where the bromine is replaced with a magnesium bromide group (MgBr). 4. **Reagent C (MgBr2/ether)**: This facilitates the formation of the Grignard reagent. 5. **Step 3**: The Grignard reagent is then treated with formaldehyde (H₂C=O), leading to the formation of an alcohol with an additional methylene group. 6. **Reagent G (1. H₂C=O 2. H₃O⁺)**: The addition of formaldehyde followed by acid work-up (H₃O⁺) results in the alcohol product. 7. **Step 4**: Finally, the TMS protecting group is removed, yielding the final product, an alcohol with a newly introduced hydroxymethyl group at the position where the Grignard reaction took place. The other reagents mentioned in the diagram include: - **Reagent B (TMS-Cl/pyridine)**: This is another method of introducing the TMS protecting group, using TMS chloride instead of TMS-OH. - **Reagent D (Mg/THF)**: Typically used for preparing Grignard reagents. - **Reagent E (H₃O⁺)**: Acidic work-up used to quench reactions. - **Reagent F (1. (CH₃)₂C=O 2. H₃O⁺)**: Alternate addition of acetone, followed by acid work-up, which can introduce additional structural changes. This sequence demonstrates functional group transformations using protection and conversion strategies in organic synthesis.
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