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Kritik Assignment 3 Question 3. 6 marks total. a) An E2 reaction will occur when the beta hydrogen and the leaving group are anti-coplanar. In the following reaction only one tetrasubstituted alkene is produced. Complete the wedge and dash drawing (structure B) and draw the tetrasubstituted final product (structure C). 1 mark for correctly adding groups to the middle diagram. 1 mark for correct alkene. CH3 CH3 Br Br CH3ONa CH3OH Br b) Draw the substitution product produced in the following two-step reaction. The nucleophile selectively reacts once in each step. Is the product optically active? 1 mark for correct substitution. Use dashes and wedges to show stereochemistry. 1 mark Would a solution of the product be optically active? CH3C complete by adding substituents with correct stereochemistry 1. KCN (1 equiv.), DMSO 2. CH3CH₂ONA, CH3CH₂OH Br OSO₂CF3 complete by adding substituents with correct stereochemistry major product(s) Would a solution of the resulting mixture be optically active? Yes c) Draw the substitution products for the following two step reaction. The nucleophile selectively reacts once in each step. Is the resulting product chiral or achiral? 1. NaN3 (1 equiv.), DMF 2. CH3SH 1 mark for correct substitution products. Use dashes and wedges to show stereochemistry. 1 mark Would a solution of the resulting mixture be optically active. No 3

Kritik Assignment 3 Question 3. 6 marks total. a) An E2 reaction will occur when the beta hydrogen and the leaving group are anti-coplanar. In the following reaction only one tetrasubstituted alkene is produced. Complete the wedge and dash drawing (structure B) and draw the tetrasubstituted final product (structure C). 1 mark for correctly adding groups to the middle diagram. 1 mark for correct alkene. CH3 CH3 Br Br CH3ONa CH3OH Br b) Draw the substitution product produced in the following two-step reaction. The nucleophile selectively reacts once in each step. Is the product optically active? 1 mark for correct substitution. Use dashes and wedges to show stereochemistry. 1 mark Would a solution of the product be optically active? CH3C complete by adding substituents with correct stereochemistry 1. KCN (1 equiv.), DMSO 2. CH3CH₂ONA, CH3CH₂OH Br OSO₂CF3 complete by adding substituents with correct stereochemistry major product(s) Would a solution of the resulting mixture be optically active? Yes c) Draw the substitution products for the following two step reaction. The nucleophile selectively reacts once in each step. Is the resulting product chiral or achiral? 1. NaN3 (1 equiv.), DMF 2. CH3SH 1 mark for correct substitution products. Use dashes and wedges to show stereochemistry. 1 mark Would a solution of the resulting mixture be optically active. No 3

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 2E
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Kritik Assignment 3 Question 3. 6 marks total. a) An E2 reaction will occur when the beta hydrogen and the leaving group are anti-coplanar. In the following reaction only one tetrasubstituted alkene is produced. Complete the wedge and dash drawing (structure B) and draw the tetrasubstituted final product (structure C). 1 mark for correctly adding groups to the middle diagram. 1 mark for correct alkene. CH3 CH3 Br BrH CH₂ONa CH3OH Br b) Draw the substitution product produced in the following two-step reaction. The nucleophile selectively reacts once in each step. Is the product optically active? Br CH ₂0 complete by adding substituents with correct stereochemistry 1 mark for correct substitution. Use dashes and wedges to show stereochemistry. 1 mark Would a solution of the product be optically active? 1. KCN (1 equiv.), DMSO 2. CH₂CH₂ONA, CH3CH₂OH ***** OSO₂CF3 complete by adding substituents with correct stereochemistry 1. NaN3 (1 equiv.), DMF 2. CH₂SH major product(s) Would a solution of the resulting mixture be optically active? Yes c) Draw the substitution products for the following two step reaction. The nucleophile selectively reacts once in each step. Is the resulting product chiral or achiral? 1 mark for correct substitution products. Use dashes and wedges to show stereochemistry. 1 mark Would a solution of the resulting mixture be optically active. No Yes 3 major product(s) Would a solution of the resulting mixture be optically active? No
Transcribed Image Text:Kritik Assignment 3 Question 3. 6 marks total. a) An E2 reaction will occur when the beta hydrogen and the leaving group are anti-coplanar. In the following reaction only one tetrasubstituted alkene is produced. Complete the wedge and dash drawing (structure B) and draw the tetrasubstituted final product (structure C). 1 mark for correctly adding groups to the middle diagram. 1 mark for correct alkene. CH3 CH3 Br BrH CH₂ONa CH3OH Br b) Draw the substitution product produced in the following two-step reaction. The nucleophile selectively reacts once in each step. Is the product optically active? Br CH ₂0 complete by adding substituents with correct stereochemistry 1 mark for correct substitution. Use dashes and wedges to show stereochemistry. 1 mark Would a solution of the product be optically active? 1. KCN (1 equiv.), DMSO 2. CH₂CH₂ONA, CH3CH₂OH ***** OSO₂CF3 complete by adding substituents with correct stereochemistry 1. NaN3 (1 equiv.), DMF 2. CH₂SH major product(s) Would a solution of the resulting mixture be optically active? Yes c) Draw the substitution products for the following two step reaction. The nucleophile selectively reacts once in each step. Is the resulting product chiral or achiral? 1 mark for correct substitution products. Use dashes and wedges to show stereochemistry. 1 mark Would a solution of the resulting mixture be optically active. No Yes 3 major product(s) Would a solution of the resulting mixture be optically active? No
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