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CHE 8A: Quiz 5/9 Study Guide

by: Mackenzie Hayes

CHE 8A: Quiz 5/9 Study Guide CHE 8A

Mackenzie Hayes

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This Study Guide Compiles the important sections of the past 2 weeks notes for the quiz
organic chemistry - brief
Sarah Lievens
Study Guide
organic, Chemistry
50 ?




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This 7 page Study Guide was uploaded by Mackenzie Hayes on Thursday May 5, 2016. The Study Guide belongs to CHE 8A at University of California - Davis taught by Sarah Lievens in Summer 2015. Since its upload, it has received 119 views. For similar materials see organic chemistry - brief in Biological Sciences at University of California - Davis.

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Date Created: 05/05/16
CHE 8A: Quiz 5/9 Study Guide ● Cycloalkanes​ → longest chain = ring ○ Number so you get the lowest possible #’s on substituents ○ If a tie → go ABC order ● 1 substituent: ○ Methyl cyclohexane → only 1 substituent, has to be C #1 ○ Writing 1-methyl… would be unnecessary ● 2 substituents: ○ 1 substituent will be #1 and the other as low as possible ○ TIE: so we go with ABC order ■ * 1-chloro-3-ethylcyclopentane * ■ X 3-ethyl-1-chlorocyclopentane X ● 3 (or more) substituents: ○ Aim for lowest possible numbers ○ If 2 or more are on the same C, ALWAYS make that C #1 ○ 3-tert-butyl-1-fluoro-1-methylcycloheptane ● Boiling Points: ○ Measure of energy it takes to break up all intermolecular forces ■ Not the molecules themselves ○ Higher boiling point (BP) = more intermolecular forces ■ More “sticky” to itself ● Alkanes:​only one kind of Intermolecular Force (IMF) ○ London Forces / Dispersion Forces ■ Temporary dipoles; very weak ■ Move around like at a party, leaving an average overall force ○ London Forces: r andom motion of e- clouds → create temporary dipole ■ Increase with larger molecules = more stuff = more e- ■ ↑mass ↑BP ■ Increase with greater Surface Area (more dipole to contact) ■ ↑Surface Area ↑BP ● Haloalkanes:​increased BP when compared to Alkanes ○ Permanent polar bonds / permanent dipole ○ Bigger orbitals = squishier = polarizable ○ Adding a non-C element → ads a permanent dipole ■ Increases BP: Stronger IMF =​ipole/dipole, polar interactions ○ ↑Dipole ↑BP ● Hydrogen Bonds: strongest IMF ○ Between H and O,N, or F (with lone pair on O,N,F) ○ Huge dipole moment bonding to H ■ H2O → 2 H-Bond per O → BP 100°C ■ NH3 → 1 H-Bond per O → BP -33°C ■ CH4 → 0 H-Bond per O → BP -167.7°C ● Solubility: ○ How a molecule interacts with a different substance ○ How 2 substances dissolve together ○ Like dissolve Like ■ Different IMF = less soluble ○ Highly polar (H2O):can dissolve Polar things ■ Amines, alcohols, carboxylic acids, ketone esters ○ Non-Polar (alkane, oil)can dissolve non-polar ■ Alkanes, haloalkanes, alkenes, alkynes ○ Slightly Polar (ether)can dissolve most stuff at least a bit ■ Ethers, ketones, esters, haloalkanes, amine, alcohols ○ Ions:​dissolve in H2O ● Into 3 Dimensions: ○ 2 extreme structures ○ (solid triangle = to us, dashed = away from us) ○ Staggered Rotamer: ■ Essentially looking at angle from the side ■ Angle btwn H’s on 2 different C’s = 60 degrees = torsional angle ■ Center = C1, Ring = C2 ○ Eclipsed Conformer: ■ All C-H bonds lineup ■ H’s directly eclipsed by one another ■ 0 degrees torsional angle ○ Skew Angle = a ​nything else (any other torsional angle) ● 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) ● 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 ○ 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 ● 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) ○ 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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