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Br (a) H. and Br CH, and "Br Br CH, Br. (e) and

Br (a) H. and Br CH, and "Br Br CH, Br. (e) and

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter12: Chirality
Section: Chapter Questions
Problem 7CTQ
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1. Consider the following pairs of structures. Designate each chirality center as (R) or (5) and identify the relationship between them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use handheld molecular models to check your answers. HG (a) Br and and CH H,G H (b) and CH, Br Br 'F (k) and Br CI Br (e) and CH, CH, CH CH, CH, H- -H- CH and H- -Br (d) and FCH CH, CH, Br H CH, and (m) (e) and H. Br CH, and (m) and Br CH (o) and nd and and and
Transcribed Image Text:1. Consider the following pairs of structures. Designate each chirality center as (R) or (5) and identify the relationship between them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use handheld molecular models to check your answers. HG (a) Br and and CH H,G H (b) and CH, Br Br 'F (k) and Br CI Br (e) and CH, CH, CH CH, CH, H- -H- CH and H- -Br (d) and FCH CH, CH, Br H CH, and (m) (e) and H. Br CH, and (m) and Br CH (o) and nd and and and
2. Designate the (R) or (S) configuration at each chirality center in the following molecules. HN CI CI SH SH Br Br CI 3. A compound D with the molecular formula CGH12 is optically inactive but can be resolved into enantiomers. On catalytic hydrogenation, D is converted to E (CSH14) and E is optically inactive. Propose structures for D and E. 4. For the following molecule, draw its enantiomer as well as one of its diastereomers. Designate the (R) or (S) configuration at each chirality center. CI CH3 Br 5. (a) Draw a conformational structure for the most stable conformation of trans-1,2- diethylcyclohexane and draw its mirror image. (b) Are these two molecules superposable? (c) Are they interconvertible through a ring "flip"? (d) Repeat the process in part (a) with cis-1,2- diethylcyclohexane. (e) Are these structures superposable? (f) Are they interconvertible?
Transcribed Image Text:2. Designate the (R) or (S) configuration at each chirality center in the following molecules. HN CI CI SH SH Br Br CI 3. A compound D with the molecular formula CGH12 is optically inactive but can be resolved into enantiomers. On catalytic hydrogenation, D is converted to E (CSH14) and E is optically inactive. Propose structures for D and E. 4. For the following molecule, draw its enantiomer as well as one of its diastereomers. Designate the (R) or (S) configuration at each chirality center. CI CH3 Br 5. (a) Draw a conformational structure for the most stable conformation of trans-1,2- diethylcyclohexane and draw its mirror image. (b) Are these two molecules superposable? (c) Are they interconvertible through a ring "flip"? (d) Repeat the process in part (a) with cis-1,2- diethylcyclohexane. (e) Are these structures superposable? (f) Are they interconvertible?
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