CHEM-239 Organic Chemistry-II

CH-18 HW (Due Oct 16 via BBA/9PM) (30à3 Points)

Octavius Lonis
Name ______________________________

1. Elaborate in your own words (2 pages maximum) the highlights of Lecture-13 with a
few representative examples discussed in the class (All Organic Synthesis Problems &
Reaction Mechanisms, if applicable, MUST be
documented). 10 points
Some mechanisms Were
gone
over
ex)
-
- - -- -x
ex 10) 0
-I 10)
%Y 457
-- --

+ + +

- o s
--

↓ Brhr --
-- -

Be
Als 101 -o

%
-

t e pri
- * on

-
& For -
Mg /Ether
L 0S
↓soci
g
- O

- /not ex -" -
-
Agel lowe
N
Br
-

is - I I
-- I
--
u ⑭
NazCrOn dee2
L -

DS I es
/

H2SO4
L
--
I on
ex ! ex el
L2
-
L or
I
- --
II
L - I
10)
Agels O
E--
-I
--
--

&
-
-

↓ Brethr
he/s H30
1hr
--Br My
enz-c-ane ,
-
- --7 ex) /
10, E 10)Chot
-]4 10 I
-
be e
-
n
a
- -
ma 1-0] x

AlCly

You Ether - -

90 Br
*
1
were
t pat Easi O
 Next
Cl
Nucleophilic Aromatic Cubstation Was discussed
I & Example without
N NaOH
1
- NR
Using tomatical
an
[Jw
Na
zNaOH 0
H +
are /-
e -
,
--
-
10!
3600

ex) e i
on

(NO2 50 2 k)
,

,
a !
ex) &
Fon
-

I X /
10)
->
II)
/
-

1)
- -
d

= Go
-
G

-
BenzgneIntermediate
Br

I ⑳
⑦

ne1 + Ne

was
-3 >
Na NHz
-

-I
L
- - >
L
-

dis
duas
Ne

J 10)
I- - rn, -
:
③-
.- -o sor

its
is
↓ HyN
:

*Gre
in
->
-No e

[x] I
Be

ex X
Lo m
dus
dide chain Oxidation

3
X-CH3
10
-- CH,3 co

01 or I I
X-
10)
-on

/ CH2CH2C2CH3 E
1
-

C Benzoic tech

A
- on

H
-> 101
KMON -Yor
Another Reaction

Xengorlong
--coct
(0) Hot
-
CNO2 ,
Y
, and
 2. Elaborate in your own words (2 pages maximum) the highlights of Lecture-14 with a
few representative examples discussed in the class (All Organic Synthesis Problems &
Reaction Mechanisms, if applicable, MUST be Deaction
Grignard *
documented). 10 points R -
Br My R g-r
Keytones Cesis was discussed tr do
Aldehyches
=

I
=

and
sy
n
.

Using ArignardRagen
t-
I E
n
04 -* - on
- r

R- ↑
R · 2 Buli
-
R- c
-

R Br
My -Bu
MyX
R- I
.
-

Ener
--

Emir
H
Ether
of ex -Br then
Hydration Alaynes -
↓
R-echg Keystone R-cn2 R-enz-cU-

a truly
R-c = CH
-
MgBr
Lo Lit
2
↑ --/ ↓
Manconino & -

Ha
R-cr2 - - or
yerOTR-cHz-en-On
-

H2SO4
- Se

ex) ⑦④ CHICEN
R-Br Ase Re Br
My-->
Mottimancornikov

! rg ⑦
Ether

R-ezenu (
Br

HzC- e R

cus-
H30
-

Not endt
- -

0Onc -R1

C4z I
R -

↓
- -

Keytone- ↓ &
end 0 NH2 - -

⑰ n
R-CH2-C Nt n
=

f
Hantemization
i - 43 ec R I
-

Ayusis
-

J
Keylone us 0
-
in
II
nz-
zai R-e-ally
Cre H20

Sew
R -o n
CHz-CN
R-CH--11
R-
- -

ex
as elie
My
!
V

- Lie
-
m -
·
e-
Lie t
recon R-Br
X ⑦
CHz-CEN
-
dus ex
Ether
R
MgBr -

⑱
enzlie
2
④
B
43s
-
-
R Mg
 WittigReaction sp
T 0
R-chBr I -- R
- -
=

Pph3

de
resona

- p- ⑲
↓
o
② Buti
Base
Astrong & --
- -

/ -R
pphs
② Buti

Wittig Mechanism
--- -] Wittig phaP=-mc
gi
oh
Polis
· Lit
Complex
Sin
0
↓
=

he va

Mum
e C bond
= plea
au en-PP2 -
T
-

/ O
⑦

R
.

Wolff-Kishner Reduction Similar to This] ⑧

--R Na
R-cHz-
R
-archch---al -
401
m
101 -
AICI
--
e
40t
↓

Xeroa
-x
of 1
O
d
on
I

-
H-
C
-
S"
2
/ N-a-
M
& -
-
o
-

-
⑰

-
-
> =
O NH2NH2 N -

NZ I N-wrz
-
d > =

-
r

we
-
y
·
con n'

A
ex)
* I e
KOH

f.
*

0 0
-

---
11
i
1
--

0
11
↓Ne1I KON
-2

N
-
↓

Protection/Deprotection Mechanism 4

S
o
-

A in
as /
I ⑰

=
-
R-on - /
o -2

if
·
-Ok
I = 0
e

*
Y* R 420 ⑰ & O -

on
Ho
- -on 0 H
40
/
-

&
I I
/
-
-

= 0 - &
-> / -
↓ OR
On
on
OR
2'ROH Int
0 X: 7
*

> =

D
 3. Elaborate in your own words (2 pages maximum) other important aspects of Chapter-18
(not discussed in the class) with a few representative examples. 10 points

Add one more page, if necessary

The nomenclature for Ketones and

Aldehydes is
very important the
to know .

Systematic
names of ketones
by replacing final-e
are derived name
the in alane

with She
one
alane" The final of
"

Aldehydes
For
.

name "ananome -e
the alame
.

name with ,
of d
-al Im Aldehyde Carbon 2tthe end

chainsoit i numberttheAldehyde group

.

is
hithe
of large
is substituent

Keytone
Cr 3
i
⑭
-CH3
s
O I - -en

en _ "-c-CH2 enz-an-en-a43 -
, ,

4-dimethylpentan-3-one 1-phenylpropan-1
-
one
butan-2-one 2
,

Aldehy des
CHz-2
⑭
H CHzCh,
By
z-cr-CH
cust XY-aro
Cyclohexanecerbeldehyde
-

↑ bromo-3-methylheptanal .

Shere are common Aldehydes and adid

of
Paints(PhysicalProperties)
some ames

Carboxylic said Aldehyde Las boiling

HyTheand
⑭ -n of Ketones
Aldehydes
a re e
a

Smic
o
-
-

formaldehyde
There arelower ling an
acid

-*
ue
en -

Acetaldehyde Molecular Weight .

O
au--r C4g0-CHaCs
curopionaldehyde CHICHaCHeCHy
-

or

Cropionic
an Chan
-
- -

butane methoxyel
acid
bpO
VS-
bpac

ChyCHz ON

Propan-1-01
bp 94°