problem set 3 key - orgo

problem set 3 key - orgo - Monda y Nig ht Problem Set 3 M...

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Monday Night Problem Set 3 M L E C U L A R M O D E L I N G continued…. . 6) Construct a model of cyclohexane: a) Note the flexibility in the structure. Arrange the atoms into a puckered “chair” conformation. b) On the more detailed picture below, circle the axial hydrogen atoms. H H H H H H H H H H H H c) Select any C-C bond in cyclohexane and view along that bond axis. Are the hydrogens staggered or eclipsed? ___ All H’s are staggered. ________ d) Based on your answer to part c), why is cyclohexane puckered (as opposed to planar)? 2 reasons: 1) Attachments to all C’s are staggered – no torsional strain! 2) Puckering causes the bond angles to contract to a perfect 109 o e) Replace one of the axial hydrogen atoms with a methyl (-CH 3 ) group. Now, do a “ring-flip” with your model – make the headrest the footrest and vice versa. The methyl group should now be equatorial. Which looks like a more stable conformation to you, the cyclohexane with an axial methyl group or the
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This note was uploaded on 04/29/2008 for the course CHEM 221 taught by Professor Fillinger during the Spring '08 term at Ithaca College.

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problem set 3 key - orgo - Monda y Nig ht Problem Set 3 M...

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