The Fischer projection formula of (S)-proline is to be given. Concept introduction: In Fischer projection formula, the amino acid molecule is represented by placing the COO- group on the top of the chiral carbon. The configuration in which the NH 3 + group is placed on right is said to be D configuration while that which has NH 3 + group on the left is called to have L configuration. Based on sequence rules, the four groups attached to the chiral carbon are arranged in the order of priorities. While viewing the molecule from the side far away from the group of lowest priority, if the arrangement of first highest priority, second highest priority and third highest priority is clockwise the molecule is said to have R configuration and if the arrangement is anti-clockwise the molecule is said to have S configuration. To draw: The Fischer projection formula of (S)-proline.

Question

. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

Answer 1

Question

Chapter 26.SE, Problem 31AP

Interpretation Introduction

Interpretation:

The Fischer projection formula of (S)-proline is to be given.

Concept introduction:

In Fischer projection formula, the amino acid molecule is represented by placing the COO- group on the top of the chiral carbon. The configuration in which the NH₃⁺ group is placed on right is said to be D configuration while that which has NH₃⁺ group on the left is called to have L configuration.

Based on sequence rules, the four groups attached to the chiral carbon are arranged in the order of priorities. While viewing the molecule from the side far away from the group of lowest priority, if the arrangement of first highest priority, second highest priority and third highest priority is clockwise the molecule is said to have R configuration and if the arrangement is anti-clockwise the molecule is said to have S configuration.

To draw:

The Fischer projection formula of (S)-proline.

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. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

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