110a Exam 2 Review SheetFall Semester 2013 Review Session: Wednesday, October 2, 7:00 PM, Hahn 101 Exam: Friday, October 4, 7:50 AM, SN Aud

bankercordMechanics

Oct 27, 2013 (3 years and 9 months ago)

70 views





110a

Exam 2

Review Sheet

Fall Semester 2013

Review
Session: Wednesday, October 2
, 7
:00 PM,
Hahn 101

Exam: Friday, October 4, 7:50

AM, SN Aud



Chapter 4:


IUPAC nomenclature for C10 branched alkanes, alkyl halides,
alkenes, alkynes,
and alcohols; fragment
names: propyl, isopropyl, sec
-
butyl, isobutyl, tert
-
butyl, pentyl, neopentyl; IUPAC nomenclature for
cycloalkanes, including cis
-

and trans
-

descriptors; IUPAC nomenclature for bicyclic alkanes; physical
properties of alkanes

(VDW in
teractions, effect of branching on boiling point, alkanes with a “useful”
boiling point, density relative to water)
; thermochemical (comb
ustion) analysis of ring strain and ring
strain trends for C3
-
C14 rings;
conformational analysis; sigma bonds; ethane, Newman projections,
torsional strain and its origin, conformational isomers, room temperature picture of ethane, staggered
conformation, eclipsed conformation, 2.8 kcal/mol barrier in ethane; butane conformatio
nal analysis,
gauche vs. anti conformational isomers and free energy difference between them, repulsive VDW
interactions, room temperature picture of butane, reasons for different barrier heights (3.4 vs. 5.5) on
rotational trajectory of butane; origins of

ring strain in cyclopropane, cyclobutane, and cyclopentane;
reasons for conformational flexing in cyclobutane and cyclopentane
; preferred conformations of
cy
c
l
opentane; preferred (chair) conformation of cyclohexane, axial vs. equatorial bonds, interconver
si
on
via ring inversion;

conformational analysis of intermediates along the ring inversion trajectory
-

pick one
or two unfavorable interactions (e.g., torsional strain) for each, symmetry of the twist conformational
isomer; kinetics vs. thermodynamics;



=
-
RTlnKeq; conformational analysis of substituted
cyclohexanes, 1,3
-
diaxial interactions (repulsive VDW interactions in the ring system); what is the
relationship between methylcyclohexane thermodynamic behavior and butane conformational analysis?;
reaso
ns for increasing degree of equ
atorial preference for bromine
, methyl, and tert
-
butyl substituents on
cyclohexane; tre
nds in cyclohexyl halides
; methods

for synthesizing alkane
s from alkenes
-
catalytic
hydrogenation & index of hydrogen deficiency
.



Chapter

5:



stereoisomers, enantiomers, chirality, achirality, stereogenic center, chiral center,
diastereomers
, Van't

Hoff; Pasteur; tests for chirality, methods for differentiating enantiomers
-

optical activity, enzymes
--
how?; Assigning configuration and designating stereochemistry: the
R
/
S

system, the D/L system, the +/


system, the
d
/
l

system. Specific rotation and
enantiomeric excess
; racemic mixtures; the thalidomide
story
; chemical correlation as a means of assigning configuration; absolute and relative configuration;
understanding of how diastereomers have different physical properties; meso compounds; Fischer
pr
ojection formulae; optical resolution.