worksheet3 - Chem 8A. Lecture on Shape and Movement...

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Unformatted text preview: Chem 8A. Lecture on Shape and Movement (Conformations) of Organic Molecules, October 19th Concepts to Know bond rotations for single bonds chair conformations sterics ring strain equatorial and axial positions cis and trans isomers of alkenes E and Z naming of alkenes Skills: 1) Recognize that molecules have a 3-D shape or conformation that relates to their energy 2) Be able to draw a chair structure for a cyclohexane ring and the other chair conformation (Le. a ring flip) 3) Identify a conformation of a molecule that is more stable (lower energy) 4) Identify if an alkene is cis or trans (and relate to E or Z) Practice Problems: 1) Rank these cycloalkanes in order of stability. Justify your answer in terms of sterics and strain. D 00A 2) Draw the Newman projection of the following compound looking from the perspective of the arrow. (aka the CZ-C3 bond) \ Draw the three staggered conformations and the three eclipsed conformation. Do the three staggered conformations have the same energy? Do the three eclipsed conformations have the same energy? Identify the highest and lowest energy conformations. 3) Draw a chair conformation for each of the compound below. Label the axial and equatorial groups. Q< OH 3 ’2 //\ QOOH 9 OH Br ~O< Cl OH “9‘ Q 4) Below are the chair conformations of various substituted cyclohexanes. Draw the other chair (Le. do a ring flip). 3% Cl 3 XZU‘LXLJL 5) For each compound below, draw the most stable chair conformation. Justify your answer. 6) For each of the compounds below, determine whether the double bound is cis or trans. I 1 Indicate whether each of the following in an E isomer or a Z isomer. R @ Et Br 11: 7) B I 8) Draw and label the E and Z isomer for each of the following. CH3CH2C —CHCH3 CH3 CF3CH= CCH=CHCH3 CHZCHZCH3 ...
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This note was uploaded on 06/27/2010 for the course CHE CHE 8A taught by Professor David during the Spring '09 term at UC Davis.

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worksheet3 - Chem 8A. Lecture on Shape and Movement...

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