Organic Concepts

Homework

Solutions to HWS-6-Organic Concepts

 Chemistry Organic Concepts Home Work Sheet-6

1- .

SNZ SNI .

(a) RI doubles & RI remains same

#

(b) RI increases 4 times & RII doubles

SNZ : correct

2°
should be EZ ( wrong)

EZ

More stable EZ
:
conjugated
cuzCU=cnz
Note : mez.co : sterically hindered
bulky base
is formed Organic Concepts gives
Hoffmann's product
3. Identify the products .

activated ;
is Ring II
1- M M Ring I
-
-
-

• o
is deactivated ◦

SE
y

I F- Br - -0 -
É -

ome

Me
Cnaior
SNI EL EL Me

0-4 aq cuz
1-132
=
1° -=

#
:c
vinyl SNZ -
OH
allylic I product
<n SNZ Rxn , only
is formed .

B ✗ 13 a

tip
° "
r

OH
g- r

•
8- Lactone
4.

Organic Concepts
4*91 .

I
°" Brz
C6Hq only one isomer is formed
Me Fe
COOH
so Es '
is meta -
isomer
•◦

(B)
4cm) (isopttnatic acid )

(A) .
COOH
Et -

COOH (C)
Cm ]
#

Fe COOH
Br

002 It
'
.
both atoms are attached to ring

C- M )
Cl Cl
Nah
Goltz c , GHz 1 C6H4% Notz
C- ) Coon Cao I
,
me ,

C- M) only 1 isomer
CI
it it is
Me CI means
p isomer
-
•

COOH C1
-

-
( O) Ct
NaOH Noz
Cao /
Cl
g,

Organic Concepts Cl
Cl
 & Products
5. Identify Major minor .

H " "
1 H de
④F
.
.

B, =
KOH :* ph
µ↳ ph ph

H
ph
H
E2
Cnojor)
is not
formed
⑦ Hj Met Tert butoxide
MezCÑN+a=_ cuz
.

# due to being
2-
Br
sterically kindred (Major
Mezcotl, #
fails to abstract Me
Me
Ez
2%-013-4 Me

(3) Hp (Minor 1)-

Me
(Minor -2)
it is
Hough
the more stable )
Br the

3
Et5Na
, 0
Eton #
,
0 t 0
Me EZ

Me
Cmajor ) Me
(Minor
conjugated
Organic Concepts
 5h
4. +
Me OH
ale
F = . Kou
cnajov) (Minor)
•
F- is a
poor leaving group
(as it is a
strong base
)
•
as a double bond
result ,
character is not formed cis
TS and 1°C
acquires 8-
#

(carbanion) character & it is

more stable As a result
.

Hoffmann 's
product is Major

P
me
5- "
% H ak.ko.gg Observe that both
Hp are in same plane
""
""
"' Br so EZ does not occur here .

think about EI here solvent

Casalcohol is
É= Me (Ez)
• we can
)
Hz Me Me

→
'
'

(
+
EI)
-
me -
me

Organic Concepts
 & Products
6. Identify Major minor .

1 I Ht
.
+ +

OH ⇐ 1)
Cmajor) Cpninor)
2 3
04 3
2. 1. Ht (EI) +
,
-

z
4
£
#
' i 6 4 I 5
g-
6
+
2. -

H2O

(minor) + ( ajor)

3.
me
1. H3P04
( EI)
Ñ) the
-

+ -
Me
Eu Shift
, 3%-1
OH 2 .
-

H2O

Me Me
- + _

(Minor ) (Major) : Moreno .

of ✗ -4

Organic Concepts
 acidic
°
£"
-1%-4
d- EICB
4. É
gu ,
-

cuz
-
-
n
cuz -
In
OH
TOH
poor leaving
group
cuz=Eu-É
P
-
u cnzɥ
acrylaldehyde -04
564
acidic
#
(E9cb)
↑ slow
&
5. ✗
11 0-4
similar to above
9h cuz n exactly
- - -

A-
Oh
poor leaving
group _ En -_Eu -1%-4
Cinnamaldehyde

Organic Concepts
*

CH
] NaOH
( )
P :
C6H4( dicarboxylic acid
g- cuz cool
•

3
C6Hq
C6H4fco☐µ
-

Br it should be
Br
•
#
e cuz
-

Nam
.
it means that (D)
3 1=2
C6Hq 1- CHI
}
should be a di substituted
-

COO Na derivative
NaOH
C6HsCUz (R)
Cao, (s)
COOY

c43@C6Hqfaooy0CJC8H4O3C6H4Icuz2.Re
- .

d%I
Ht

anhydride 9AM
-%°
pthalicacids
-

it should be 0
-

( pthalic acid
)
COOH

③ (T)
Coon

Organic Concepts