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Organic chemistry 2 ALL EXAMS REVIEW

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Course
CHEM231

Institution
Montclair State University

this Organic Chemistry II exam review covers key topics like reaction mechanisms involving carbonyl compounds, aromatic substitution, and the chemistry of carboxylic acids and their derivatives. It includes multi-step synthesis strategies, advanced spectroscopy (NMR, IR), and the reactivity of conj...

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Organic Chemistry 2: ALL CLASS NOTES AND EXAMREVIEWS

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1. Other - Organic chemistry 2 notes
2. Other - Organic chemistry 2 all exams review
3. Class notes - Organic chemistry 2 class notes
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, Exam / review

Chapter 14 conjugated compounds : and UV spectroscopy

Conjugated compounds
↳ compounds with
alternating double and single bonds
↳
They by using base induced elimination of
are made HX from an Allylichalide
↳ The middle
single bond in a conjugated diene is shorter
HA Br

NBs KockHala
than a non conjugated one ↑
due to orbital hybridizati 4 HOC((Hzbe
Cyclohexene S-Bremocyclohexene 1,
3-Cyclohexadiene (76 %)
·
substituted alkenes are more Produce less heat
stable and
So they release heat when added to water
one diff btwn cony dienes and alkenes
.
is electrophilic addition rxns

1,2 & 1
,
4 addition
Sometimes conj. dienes can get 2 products and ,
one will have the alkene on the central
Carbon 1 2 1, 4
,

HBr
Nisr
-
x +

1 ,
3-butadiene It i
1 ,
2
1 4
Br 2
,

- -Br
20 %
Br
t
B Bo
d Inajor Minor
12
129134

#
2
1 ,
"

+
it [a
c Kinetic
T
therm
namic

1, 2 1 4
Kinetic and themodynamic control
,

Kinetic control : The Product of an irreversible ran. depends on reletve ratos not stability
↳ Low Product with lower Ea will form greater amounts
temp ; Irreversible .
in

thermodyname control : Product is reversable depends on Stability ,
not relative rates
↳ high temp ; reversable
.
when we have an Irreversbe lower tempran ,
product will depend relate rates . If we have a

higher temp reversable rxy , major product will depend on stability

Diels-alder cycloaddition reaction
↳ cons-dienes
undergo an addition run with alkenes to make subst Cyclohexone products·

, dienophile
diene O
diels-alder rxn =
DAR

.
5 y or #
S
↳3 butadene 3-butene-2-ove 3- Cy clohexany
methyl ketone
↳
This process is called the diels- alder cycloaddition reaction
not polar or radical
dienophile : alkene Part of DAR
(dieve cover)

*
DAR can
happen quicker when the dienophile has an EW Substituent Group Stereospecific : a single
Product Stereoisomer is formed . e

ex
alkynes can
i

·
also act as dienophiles .

can as product , trans Product

b UV Spec
Predict the following diels -
alder rxn endo (Syn) .

-1 P electrons can be shifted
by Ultraviolet light
>
-

-
Y

When "white
- light strikes
-

a cony
Molecule
. The wavelength needed for

exitation is Absorbed
The dienophile
·
has to have an ewo and can sometimes have a triple bond
Stereochemistry of dienophile Maintained during the reaction
·

the is

The Diene
·
has to have (is-like") Conformation to do DAR .

to create
Some can rotate a S-cis Conformation
rigid ones can't
·
.

·
diens are very reactive and have an s-as geometry

Diene Polymers
·
like simple alkenes , con) · diones can polymerized
-

because double bonds remain in the Polymer as-trans isomerism is possible -

Polymerizati Can be initiated by radical add
-

or

Polymereati addition
-

Occurs via 1 4
,

HOMO highest electron filled orbital
!
:

Lumo : Lowest electron Poor orbital
Y2-Ys is hom
N4-Ns is Lumo

, 15 Benzene and aromaticity
Chapter
:

CHs
#

naming
Exis
aromatic compounds :

-
a lot of aromatic compounds have nonsystemic names
O-zylene
-more substituted benzenes are named the same way as other hydrocarbons ,
with benzene as the parent
tolvene Phenal anilive benzaldehyde
name

Exc KJXN
, G

alkyl Subst benzenes are named 2 ways :

alkyl-substituted Pheny
. in

If the alkyl substituent has 6
·
or less carbons its named as an

If the
alky) substituent has than 6 carbons Its named phenyl-substituted alkone
·

more , as a .

The Cotto CHy group denzyl group and the
Cals-group phenyl group
·

is a is a

disubstituted benzenes
↳ named
by the Ortho (0) meta (m) ,
and Para(p) system
,
O-dichlorobenzene
or tho met a Para P
-C3 #i
I . &

I Eis Br
**
Bir
M-Bromofoliere p-chloroBromobenzene

benzene with more than 2 substituents are named by numbering the position of each substituent
↳
Name like any other
namey
of benzene
Stability
addition products
benzene reacts Slowly with Bra give substitution
to not
-

,

↳ all
C-c bonds at benzene have the same length
-

benzene is Planar with all bond angles at 1200

&doe
& double bonds
-All carbons are sp2 hybridized and identical 4 it electrons

1 I antaromatic
aromatic

aromaticity aromaticity
huckel
The 4n +2 rule Cyclic Conjugated follows huckels rule
·

Planar ,
-

, ,
-

for to be arematic , i has to fulfill hickes rule
a
compound
hickes rule : a compound is only crematic If I has a plather , Monocycli system of Conjugati with a total of 4nt2
electrons

-
Molecules with (4 ,
8 , 12 ...
) are anticromatic
ex .

Cyclobutadiene (n 4) is =
anti

benzene (n c) aromatic =

Aromatic lons
·

any cyclic cony. Molecule with An + 2 electrons can be aromatic even ifIts an on
,

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