MWF_14 - Organic Lecture Series CH 310/318 M LECTURE 14...

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Organic Lecture Series 1 CH 310/318 M LECTURE 14 Textbook Assignment: Chapter 6- Begin Today’s Topics: Alkenes Alkenes Grading in Progress Organic Lecture Series 2 – Uses priority rules (Chapter 3). – If groups of higher priority are on the same side, the configuration is Z (German, zusammen ). – If groups of higher priority are on opposite sides, the configuration is E (German, entgegen ). Z (zusammen) E (entgegen) C higher C higher lower lower C lower higher C lower higher The The E , Z System System
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Organic Lecture Series 3 • Cycloalkenes – In small-ring cycloalkenes, the configuration of the double bond is cis . – These rings are not large enough to accommodate a trans double bond. Cycloheptene Cyclohexen e Cyclopentene H H H H H H H H Cyclobutene The The Cis Cis , Trans Trans Isomerization Isomerization Organic Lecture Series 4 • For alkenes containing two or more double bonds, change the infix - en en- to - adien adien-, - atrien atrien-, etc. – Those containing several double bonds are often referred to more generally as polyenes. – Following are three dienes. 1,4-Pentadiene 2-Methyl-1,3-butadiene (Isoprene) 1,3-Cyclopentadiene 1 2 3 4 5 1 2 3 4 1 2 3 4 5 Dienes Dienes , , Trienes Trienes , and , and Polyenes Polyenes
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5 – Vitamin A is a biologically important compound for which a number of cis,trans isomers is possible. – There are four double bonds about which cis,trans isomerism is possible, for 2 4 = 16 stereoisomers. CH 2 OH Vitamin A (retinol) Dienes Dienes , , Trienes Trienes , and , and Polyenes Polyenes Organic Lecture Series 6 • Alkenes are nonpolar compounds. • The only attractive forces between their molecules are dispersion forces. • The physical properties of alkenes
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This note was uploaded on 10/10/2010 for the course CH 54600 taught by Professor Colorpart during the Fall '10 term at University of Texas.

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MWF_14 - Organic Lecture Series CH 310/318 M LECTURE 14...

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