TTh_7 - Organic Lecture Series CH 310/318 M LECTURE 7...

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Organic Lecture Series 1 CH 310/318 M LECTURE 7 Textbook Assignment: Chapter 4-Begin Today’s Topics: Chirality Chirality & & Configurational Configurational Isomers Isomers Notice & Announcements: Problem Set 3 posted- Due: 2/13; 3 PM Organic Lecture Series 2 Stereoisomerism Stereoisomerism and and Chirality Chirality Chapter 3
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Organic Lecture Series 3 Enantiomers & Diastereomers Enantiomers & Diastereomers • For a molecule with 1 chiral center, 2 1 = 2 stereoisomers are possible. • For a molecule with 2 chiral centers, a maximum of 2 2 = 4 stereoisomers are possible. For a molecule with n chiral centers, a maximum of 2 n stereoisomers are possible. Organic Lecture Series 4 • 2,3,4-Trihydroxybutanal – two chiral centers. –2 2 = 4 stereoisomers exist; two pairs of enantiomers. C C H OH CHO CH 2 H C C H HO 2 H C C H H 2 C C H H 2 A pair of enantiomers (Erythrose) A pair of enantiomers (Threose) Enantiomers & Diastereomers Enantiomers & Diastereomers
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Organic Lecture Series 5 • Diastereomers Diastereomers : – Stereoisomers that are not mirror images. – Refers to the relationship among two or more objects. C C H OH CHO CH 2 H C C H HO 2 H A pair of enantiomers (Erythrose) Enantiomers & Diastereomers Enantiomers & Diastereomers C C H H 2 C C H H 2 A pair of enantiomers (Threose) Organic Lecture Series • Another e.g.--2,3-Dihydroxybutanedioic acid (tartaric acid) – two chiral centers; 2 n = 4, but only three stereoisomers exist C C H COOH COOH H C C H COOH COOH H C C H COOH H COOH C C H COOH H COOH A pair of enantiomers One meso compound (plane of symmetry) Enantiomers & Diastereomers Enantiomers & Diastereomers
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Organic Lecture Series 7 Meso Meso compound: compound: An achiral compound possessing two or more chiral centers that also has chiral isomers. C C HO H COOH OH H C C H H One meso compound (plane of symmetry) Enantiomers & Diastereomers Enantiomers & Diastereomers Organic Lecture Series 8 • 2-Methylcyclopentanol HH CH 3 H H HO H 3 C H 3 H H 3 C cis- 2-Methylcyclopentanol (a pair of enantiomers) trans- 2-Methylcyclopentanol (a pair of enantiomers) diastereomers Enantiomers & Diastereomers Enantiomers & Diastereomers
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Organic Lecture Series 9 cis -3-Methylcyclohexanol (a pair of enantiomers) OH H 3 CH O C H 3 Enantiomers & Diastereomers Enantiomers & Diastereomers Organic Lecture Series 10 trans -3-Methylcyclohexanol (a pair of enantiomers) OH H 3 C HO CH 3 Enantiomers & Diastereomers Enantiomers & Diastereomers
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Organic Lecture Series 11 Compounds with the same molecular formula
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This note was uploaded on 03/18/2012 for the course CH 310 M taught by Professor Iverson during the Spring '09 term at University of Texas at Austin.

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TTh_7 - Organic Lecture Series CH 310/318 M LECTURE 7...

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