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Ochem study-guide 2

by: Adriana

Ochem study-guide 2 CHMY 321-001


GPA 3.62

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About this Document

Covers class from 9.19,2016, 9,26.2016-10.5.2016. The last week of notes 10.10.2016-10.14.2016 will be uploaded on Sunday. This study guide covers ch. 4- most of 5, the rest of 5 and ch. 6 will be ...
Organic Chemistry I
Holmgren, Steven
Study Guide
Ochem, Chemistry, MSU, study-guide
50 ?




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This 24 page Study Guide was uploaded by Adriana on Friday October 14, 2016. The Study Guide belongs to CHMY 321-001 at Montana State University - Bozeman taught by Holmgren, Steven in Fall 2016. Since its upload, it has received 54 views.


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Date Created: 10/14/16
Ochem study guide 2 Exam on 10.19.2916 Based on ch. 4-6, but anything from the last exam is, also, fair game This study guide includes notes from 9.19.2016, 9.26.2016-10.5.2016, the last week of notes 10.10-10.14 will be uploaded separately by Sunday evening (10.17.16). Overview of notes: (see more detailed notes attached) Chapter 4: Alkanes and Cycloalkanes - The structures of alkanes and cycloalkanes - Nomenclature: (in book pg. 159)  Parents names: Meth-Dec, - ane = alkane - Substituents: (in book pg. 161, 163)  Easy substituents: Parent name + -yl  Complex Substituents: count carbons- ex: isopentyl, (1-methylbutyl) - Naming:  Identify the parent chain first- generally the longest chain (doesn’t have to be linear)  Then number the carbons on the parent chain  Name the substituents - Cycloalkanes  Cyclic in structure  Basically same naming process - Naming (IUPAC) - Isomers:  Constitutional isomers: same molecular formula, differ in atom connections  Conformational isomers: same molecular formula, same order of atom connections, differ in 3-D orientation (conformation)  To determine isomeric relationship, ask: (can’t determine if in Lewis form) 1. Do they have the same molecular formula? 2. Does the order of their atom connectivity differ? 3. Does their 3-D structure differ? -Newman Projections  Only for c-c bonds, sp hybridized  Look down c-c bond to draw  Structure: front and back carbons with substituents coming off.  Staggered  Torsion angle of 60 degrees  More stable than eclipsed  Have less energy than eclipsed  Eclipsed  Torsion angle of 0 degrees  Less stable than staggered  Have more energy than staggered  Torsional strain: difference in energy between staggered and eclipsed projections  Know how to draw Newman projections in both forms (pg. 8 of week 4-5 notes) model kits are good to figure out how to draw. (In book pg. 176)  Know how to calculate how much energy a projection requires from a provided table (pg. 10 of week 4-5 notes) - Cyclohexanes  Cyclic  Heats of combustion  Bond strain: bond angle strain and torsional strain  Chair conformations (see how to draw on pg 189)  Axial and equatorial substituent positions (see pg. 1 of week 6 notes)  Ring flip: due to rotations of all single c-c bonds  Monosubstituted cycloexanes  1,3 diaxial interactions  Disubstituted cyclohexane  Cis/ trans Ch. 5: Stereoisomerism - Definition: same molecular formula, same order of atom connectivity, differ in spatial arrangement (3-D)  All conformational isomers are stereoisomers, not all stereoisomers are conformational isomers - Enantiomers (pg 217)  Stereoisomers that are non-superimposable and mirror images of each other - Terms:  Chirality center: a central carbon with 4 different substituents attached to it.  Absolute configuration at each chirality center  Figure out by: 1. Determine the priority of each group coming off the center 2. Orient the lowest priority away from you 3. 1-2-3 clockwise = R; 1-2-3 counterclockwise = S  Optical Activity (pg 227)  Enantiomers have identical physical properties  When pure, enantiomers rotate plan-polarized light in equal and opposite directions  Chiral/ Achiral  Chiral objects/molecules are not super imposable with their mirror image  Achiral objects/ molecules are superimposable with their mirror image  Achiral or Chiral? o Does it have a plane of symmetry? Yes, then achiral o Does it have a chirality center? Yes, then chiral - Diastereomers  Stereoisomers that are not non-superimposable and not mirror images of each other  Have the same molecular formula  Have the same connectivity  Have a different atom orientation  Not mirror images - Mesostereoisomers  Mirror images  Superimposable D2L resources:  In-class problem answers from 9.26-10.17  Practice exam 2 with answers  Old problem sets with answers  Skill-builders from the book  Orion problem solutions under tutorials


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