Class notes

Rotation About a bond - Organic Chemistry

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Course
CHEM 281 (CHEM281)

Institution
Simon Fraser University (SFU )

Condensed class notes from lectures about bond rotation. Includes types of strain, energy levels, and conformations.

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Uploaded on January 18, 2024
Number of pages 1
Written in 2023/2024
Type Class notes
Professor(s) David vocadlo
Contains Class 6

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↳ g. FREEly Bounds
Moms a moreCore Roe About (o)
May
Signed
no

· Bu NOT DOUBLE Or
TRULE Bowds .
This is Due To THE Difference in

HYBRIDED
androg
MORECULAR ORBUAL OB op e n s
overup
GEOMETRIES
.

& conformations EvD to End,

scroung
Rotation A b o r THE Bord .
Pi(i) Bowds

forming
Overlap side Bod
By side
Ragid
,
I more WITH RESTRICTED

MOTION .

DIFFERENT ROTATONAS
ARRANGEMENTS
AROUND A

STYM
(O) Bond ARE CALLED Conform strows

&-
NEWMAN
PROJECTIONS
ARE A
way O
Fursuserting
This Roscom Differen Conformers
may BE
Higher ab
I
G
.

or Commer

Newman
Entergy Depending
ou Stream .

CHs'
O Bond
ROTATION
&
projections
:

H Cl3
THE ACOM CLOSEST TO THE TORSIONAL STRAIN H
H

-
Depends on Torsow Dihedral Bonds of
The Bowd
Angle
Between
Angle
This is the

engle
Each Acor

Smogle
NEWER IS WHME THE HOM or . on .

Farther from THE NEWER WHEN TORSTONA STRAM Is MonrMAL THE
SPECIES is MORE STABLE And is Lower
Energy
is ,

Conformo n conformatron
STAGGERED
THE MoCH MORE SABLE THE THE
is
ECLIPSED due

If H
LOWER And Less Represe forces
Energy
To MS
H
-

I H

H
If H H H
STERIC Strain
H It
FROM
RESULTS HAN JER WAAL'S REPULSIONS BETWEEN ELECTRON CLOUNS Of ACOMS ON THE

ECLOSED Bowd of Clouds ACOMS THAT ARE
sogg GETHER
ERED TS

SINGLE
.
MERPENEDRAOn ELECTROw occurs The CLOSE TO

BodED
CH3cH3
ECLIPSE BUT NOT
DIRECTLY
I HH

Z
Highest Energy
HCH3 HCH3

CH3 HCH3
# CH3
If CH3CH3
↓
H

CHz
Chy

H H
GAUCHE

·
It
H
As
↓ Ano;

CH3
H It H
It
HH
H I

H H
CH3 CHz H HH
STERR CH3
STRAM

............
AntipEriPlanar Gauche Partially Eclipsed
TOTALLY ECLIPSED
TORsrow
ANGLE
Cyclohexane
:

Strato no
Cyclic MOLECULES Multiple conformations for 6-membered
Frogs
. Mast S t a b l e

LOWEST conformation firp"
Energy-dhre "Ring
CyclopropANE : Axist
.

CyclotExsure car

Equatorial
60 of I of u s
Angle
Strain Because 60 °

Through
°
Torstow > lots log -
intrest in an
poss
:

Angle ↓ I
Bands!
Ring-forp
different conformations :
High Energy KCAL Actually Yeforms
- + 36 The ORBNALs in THE
,

HALFCHAR HAlfCHAM
CYCLOBUTANE : ↑

> ALL C-H Bonds COMPLETELY ECLIPSED
underst

lit
HAS STRAM A TORSTONAL STRAM BUT CAN
PLANAR BY
ANGLE
WHEN MAMAZEM Nose :
COS US TRANS C

Assuming Buxterfly
conformarow :

Cyclopentane
:
al UNDERSTAND
CAUSES
STRA
FOR NEWMA

Bonds
TWIST-Bor/ TWIST-BOA ↓ CHARS
.
LKE HAS WHEN PLANAR DUE ECLIPSEDC-I
CYCLOBOXM E , TORSTONA STRAM TO

themte Envelope conformation :
By
Assuming
Ctr

CHAN
CHAR

CHz)
, H
H
WHEN SUBSTMENTS ARE In
Equatorial POSTON THE
SpECIES

flagpole
is MORE Stable Reduces MTERACTIONS Preferrentral to

HzC
.
.

OCHz
HAVE SUBSTENT Love PARS ARE
LARGER Equatorial
LITTLE STErr UNLESS present
.
VERY
.

MORE STERR Ch3
MTERACTIONS STRAN BECAUSE THE
Roup
of
PART TEMETH -

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