MWF_9 - Organic Lecture Series CH 310/318 M Textbook...

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Organic Lecture Series 1 CH 310/318 M LECTURE 9 Textbook Assignment: Chapter 3 Today’s Topics: Stereochemistry Stereochemistry -Diasteromers Diasteromers ; ; meso meso Notice & Announcements: Problem Set 3 posted- Organic Lecture Series 2 Stereoisomerism Stereoisomerism and and Chirality Chirality Chapter 3
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Organic Lecture Series 3 • 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 Organic Lecture Series 4 • Diastereomers Diastereomers : – Stereoisomers that are not mirror images. – Refers to the relationship among two or more objects. C C H 2 H C C H 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)
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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 HO H COOH OH 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 Organic Lecture Series 6 Meso Meso compound: compound: An achiral compound possessing two or more chiral centers that also has chiral isomers. C C H COOH H C C H H One meso compound (plane of symmetry) Enantiomers & Diastereomers Enantiomers & Diastereomers
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Organic Lecture Series 7 • 2-Methylcyclopentanol HH CH 3 OH H H HO H 3 C HO H 3 H H 3 C cis- 2-Methylcyclopentanol (a pair of enantiomers) trans- 2-Methylcyclopentanol (a pair of enantiomers) diastereomers Enantiomers & Diastereomers
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MWF_9 - Organic Lecture Series CH 310/318 M Textbook...

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