Class notes

Organic Chemistry 2 class notes

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Course
CHEM231

Institution
Montclair State University

this Organic Chemistry II class notes builds on the foundations of Organic I, diving deeper into complex reactions and mechanisms, such as aromatic substitution, carbonyl chemistry, and reactions involving carboxylic acids and their derivatives. The course emphasizes multi-step synthesis, advanced ...

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Uploaded on August 11, 2024
Number of pages 35
Written in 2024/2025
Type Class notes
Professor(s) Dr. john berger
Contains All classes

organic chemistry 2
orgo 2
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organic chemistry class notes

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, Book notes 07/6/2024 Chapter 14 :
Conjugated compounds and ultraviolet spectroscopy

Conjugated compounds Compounds :
with alternating double and single bonds
if different independently but if
sat. are far from each other , they react
, they're closer
together they
,
can interact

Exy(
H # H
H
- I
H

H -yay
-
2
I I H Conjugated dienes can be made by using base-
H H
H induced elimination
it of HX from an allylic halide
Conjugated
diene
non
conjugated HA Br

diene +
NBS k JC (CH3) z
hr
* because more substituted alkenes ,
24 HOC(2Hzbe
are more stable and produce less heat Cyclohexene S-Bremocyclohexene 1,
3-Cyclohexadiene (76 %)
they also release less heat when thus
PH3
+H H
A3) 0 , - ↑
are added to water H

-

stability due to orbital hybridizati
&
c -
x ↑ Hexcc2
i
is OH

H
12 Hit H
It

one
thing that separates conjugated and non conjugated diens is that in
a conjugated diene the central (middle) single bond is shorter than a non

Conjugated one
i C Hy CH CHz
CH3-CH2CHe-CHa
. .
= -
CH =

T
There are differences between 147PPm 153 ppm

13 butadiene
Conjugated dienes and alkenes in
Butane

electrophilic addition runs when you add HC
O to an alkene adds the Cl
is this a cony-clone
to the mose Subst
Carbon .

So
2-methyl propere becomes
2-chloro-2-methyl Instead at
1-chloro-2methyl

Sometimes dienes two products , and
conjugated can get one will have the alkone
on the central carbon Br
↑ ↓
~
CyrH 3-Bromo-l-butene
H
=
-

+
H 11 % 1 2-
addition
j = c +=
- H #Y ,

H
H
it H LBY H
1-Bromo-2-butene
C-
c
=
-
yH 20
H %, 1-4-addition

1 , 3-butadiene ↓ it

, B
H
H H ↑* Br
BI H ↑
Y=c -
,
- H
C-
-

c
=
-
yH
H H
ItH ↓ Br

(example) give structures of the likely products from uyn of 1 equinent HCI with

2-methyl-1 3-cyclohexdiene ,
. Show both 1 , 2 and 1 , 4 adducts

Is 4 1 , 26 1 , 4
s HCI
-
> x
L
+

[T *
132 di
Imagine a run that can
give either or both Products of Band C
rxn at low temp (4GB(GFC)

Ax
B forms faster than 1 butcis
,
more stable than
L
B C B(4G ° (GB) Kinetic control
Because B forms faster than ( (lower temp : irreversable)
A
Bis the
Major
Product It doesn't matter If Cis more (faster) L ↳ (slower)
B
,

Stable than B at an irreversible reacti
C
. Product
The

depends on relative rates ,
not stability . Such rans are said

to be under Kinetic control

If we do the same reaction at a
higher temperature ,
both Processes
ore somewhat reversable

and reached Because
Cis It does not
equilibrium is .
more Stable than B ,
C is the
major Product ,

Matter that B bas the two one
(is slower than in equilibum
. The Product of a readily reversable xn

depends on
Stability ,
not relative rates . Such rans are said to be under equilibrum control =
thermo

dynam contine

A Thermodyname contral
↑ X
B , (higher temp ; reversable)

Summary : When we have lower temps and an Irreversable run. the
major product will
be determind by relative rates depend
.
When we higher temps and a reverssbe ran. the major product will

on
stability .
Kinetic control = Lower temp and irreversable ·

Thermodynamic control-higher temp and
Reversable

, The diel-alder Cycloaddition reaction

conjugated diens undergo an addition run with alkenes to yield subst
cyclohexene products
H
i P
H =
c -
H

#Y
-
H - -
CH3
i
CHS
-
c Tolere
+ ,
Il heat

H
- H
H -c -

3-Cyclohexenyl
3-butadiene 3-buten-2-one
methyl kotone (96 %)
1.

This process called the dies alder
↳
is -

Cycloaddation reaction
not polar or radical

(diene Lover
The dienophile : alkene part of the dids Alder xn

diels alder An occurs quicker when the cherephile has an electron with drawing substituent
group.
also act as
alkynes can
dienophing
·

Stereospecific : a
single Product Stereoisomer is formed

P
endo :
Syn(cis)
iAn i
It

[Ychz
anti (trans)
a
exo :
t >
-

/j CO2CHy
-

H
Cis product

P It
H--achs
* t

Htz(
/
i &

H
-
CH3
Trans Product

Predict the following diels-alder vxn

i

"
draw the diene so that the
2nds at its 2 double bands are near the dienophile double bond ,
then form 2 single
bonds btwn the Partners Convert the 3 double bond , into
single bonds , and convert the former
Single bond of the diene into a double bond because the deenophile double bond is Cis to begin with the 2 attached
.

hydroging
Must remain Cis in the product

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