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Complete the road map problem shown below by drawing the product of each step of the reaction sequence in the boxes. HBr Mg° ether ether 1) 2) H3O* OH РСС

Complete the road map problem shown below by drawing the product of each step of the reaction sequence in the boxes. HBr Mg° ether ether 1) 2) H3O* OH РСС

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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**Organic Chemistry Reaction Road Map** **Objective:** Complete the road map problem shown below by drawing the product of each step of the reaction sequence in the boxes. **Reaction Sequence Start:** - Starting Compound: Cyclopentene (a five-membered ring with one double bond) **Step 1:** - Reagent: HBr in ether - Product: Bromocyclopentane (the double bond is broken, and a hydrogen and a bromine atom are added across the double bond) **Step 2:** - Reagent: Mg^0 in ether - Product: Grignard Reagent (cyclopentyl magnesium bromide, where magnesium inserts itself between the cyclopentyl group and the bromine atom) **Step 3:** - Reagent: 1) (an aldehyde or ketone) - Reagent: 2) H_3O^+ - Product: (the Grignard reagent reacts with the carbonyl compound to form a new carbon-carbon bond, followed by protonation to yield a secondary or tertiary alcohol) **Step 4:** - Reagent: PCC (Pyridinium Chlorochromate) - Product: (the secondary alcohol is oxidized to a ketone) **Final Compound:** - Cyclopentyl ethyl ketone **Step-by-Step Detailed Explanation of Each Reaction:** 1. **Electrophilic Addition Reaction:** - Cyclopentene reacts with HBr in ether to form bromocyclopentane. The double bond is broken, a hydrogen atom is added to one carbon, and a bromine atom is added to the adjacent carbon. 2. **Grignard Reaction Formation:** - Bromocyclopentane reacts with magnesium in ether to form the Grignard reagent, cyclopentyl magnesium bromide, creating a structure where magnesium is bonded to the carbon formerly bonded to bromine. 3. **Nucleophilic Addition with Grignard Reagent:** - The Grignard reagent reacts with an aldehyde or ketone, followed by hydrolysis (H_3O^+) to form a tertiary or secondary alcohol, respectively. 4. **Oxidation Reaction:** - The resultant alcohol is oxidized using PCC to form a ketone. Make sure to show clear intermediate structures and to follow the progression of each reaction step when completing the reaction road map.
Transcribed Image Text:**Organic Chemistry Reaction Road Map** **Objective:** Complete the road map problem shown below by drawing the product of each step of the reaction sequence in the boxes. **Reaction Sequence Start:** - Starting Compound: Cyclopentene (a five-membered ring with one double bond) **Step 1:** - Reagent: HBr in ether - Product: Bromocyclopentane (the double bond is broken, and a hydrogen and a bromine atom are added across the double bond) **Step 2:** - Reagent: Mg^0 in ether - Product: Grignard Reagent (cyclopentyl magnesium bromide, where magnesium inserts itself between the cyclopentyl group and the bromine atom) **Step 3:** - Reagent: 1) (an aldehyde or ketone) - Reagent: 2) H_3O^+ - Product: (the Grignard reagent reacts with the carbonyl compound to form a new carbon-carbon bond, followed by protonation to yield a secondary or tertiary alcohol) **Step 4:** - Reagent: PCC (Pyridinium Chlorochromate) - Product: (the secondary alcohol is oxidized to a ketone) **Final Compound:** - Cyclopentyl ethyl ketone **Step-by-Step Detailed Explanation of Each Reaction:** 1. **Electrophilic Addition Reaction:** - Cyclopentene reacts with HBr in ether to form bromocyclopentane. The double bond is broken, a hydrogen atom is added to one carbon, and a bromine atom is added to the adjacent carbon. 2. **Grignard Reaction Formation:** - Bromocyclopentane reacts with magnesium in ether to form the Grignard reagent, cyclopentyl magnesium bromide, creating a structure where magnesium is bonded to the carbon formerly bonded to bromine. 3. **Nucleophilic Addition with Grignard Reagent:** - The Grignard reagent reacts with an aldehyde or ketone, followed by hydrolysis (H_3O^+) to form a tertiary or secondary alcohol, respectively. 4. **Oxidation Reaction:** - The resultant alcohol is oxidized using PCC to form a ketone. Make sure to show clear intermediate structures and to follow the progression of each reaction step when completing the reaction road map.
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