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CHE 8A: Week 6 Notes

by: Mackenzie Hayes

CHE 8A: Week 6 Notes CHE 8A

Mackenzie Hayes

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These notes cover everything taught in lecture with images directly from the professor's notes
organic chemistry - brief
Sarah Lievens
Class Notes
organic, Chemistry
25 ?




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This 6 page Class Notes was uploaded by Mackenzie Hayes on Sunday May 8, 2016. The Class Notes belongs to CHE 8A at University of California - Davis taught by Sarah Lievens in Summer 2015. Since its upload, it has received 13 views. For similar materials see organic chemistry - brief in Biological Sciences at University of California - Davis.

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Date Created: 05/08/16
CHE 8A: Week 6 Notes (5/2) ● Cycloalkanes formula: ○ CnH2n → all C+H no ends ● Ring Strain:​ not all rings are the same ○ Energy difference btxn cyclic + linear structure ○ 2 aspects: ■ 1. Bond angle ● Wants to be tetrahedral (109.5 degrees) ■ 2. Eclipsing strain ● Wants to be staggered (60 degrees) ● 4 different rings: ○ Propane: ■ 1. Has 60 degrees =/= 109.5 ■ 2. 100% eclipsed ■ Lots of strain ~30 kcal ○ Butane: ■ 1. Has 90 degrees ■ 2. Avoids 100% eclipsing by “puckering” ● Not flat or straight anymore ■ Lots of strain ~28kcal ○ Pentane: ■ 1. Has 108 degrees ~~ 109.5 ■ 2. w/ planar: have 10 eclipsing C-H ● Also exists as puckered (increases strain) ■ Minimal strain ~6 kcal ○ Cyclohexane: ■ When flat (planar) looks awful ■ 1. Has 120 degrees ~~ 109.5 ■ 2. 12 eclipsing C-H (lots of strain) ■ → puckers into a comfortable chair position ○ Chair:​zero ring strain ■ 109.5 degrees, 100% staggered ■ (larger molecules have some ring strain ● Cyclohexanes: ○ 3 sets of parallel lines ○ Each C has 2 H’s in different relative positions ○ Axial H - parallel to axis ■ Straight up/down with the bend of the point ○ Equatorial H - point out around equator ■ Parallel to the side it doesn’t touch ○ Each C has one equatorial and one axial H (one up and one down) ● Rings: ○ Cannot rotate 360 degrees (can’t turn inside out) ○ Can rotate partially - ring flips ○ If substituents aren’t just an H - different energy levels ■ Prefer to be equatorial ■ If more than one or a tie, the larger goes on the equatorial (5/4) ● Look at molecules and molecular formulas = what molecules are present ○ Isomers → same formula / different molecules / different properties ● Constitutional Isomers: ○ Different bonds / different names ● Stereoisomers: ○ Same bonds / different orientations ○ Different shapes / different properties ○ Different prefixes but same overall name (cis/trans/R vs S/E vs Z) ○ Different Kinds of Stereoisomers: ■ Diastereomers: ● Same bonds / not superimposable / not same molecules ● Not exact mirror images ● Totally different properties (fraternal twins) ■ Enantiomers: (relationship between 2 molecules) ● Same bonds / not superimposable / not same molecule ● Exact mirror images (left vs. right hand) ● Nearly identical properties (BP / Solubility) ● Vary in optical rotation with other Chiral molecules ● Chiral: (inherent property) ○ Have enantiomers but are overall asymmetrical ○ To have a stereoisomer: need inherent asymmetry ■ Alkanes: do not rotate around double bonds ■ Rings: can’t rotate 360 degrees ■ Can get C​hiral Carbons:stereocenters ● Specific point that is inherently asymmetrical ● Chiral Center: ○ Need asymmetry / cannot rotate to produce a mirror image ○ Takes 4 different groups on the same sp3 Carbon to be Chiral ■ Can’t match or superimpose ■ Molecules themselves can be chiral ● But can also be enantiomers ● (molecule is asymmetrical but it also has a reverse twin) ○ Can identify Chiral Centers on larger molecules ■ Often have a wedge / dash if orientation is known ○ A molecule can be overall achiral but still have chiral centers ● If we have a chiral center, how do we know where it points? ○ Assign R vs. S ○ 1. Assign priority to each of 4 groups around C ■ Highest atomic # ■ Double bonds count as 2 of that molecule, triple as 3 ○ 2. Lowest priority in the back (always H) ○ R = clockwise = right turn ○ S = counterclockwise = left turn = sinister


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