Organic Concepts

Homework

Solutions to HomeWork-Sheet-5

HomeWork-Sheet-6
 Chemistry Organic Concepts Home Work Sheet-5 Solutions

Errate in HWS -4 - Solutions :

I Me Me Me
hBr 4 5 5

En cuz
4 +
cuz TCB
-

Ch =
1 .

,
,
-1

3
'
2
#2 Me 3
Br
Br
-

tnz : is missing in i

CM3
both answers

II.

Me H+ 5
Me
5. 4 6
I
cn =
cuz tn OH cuz
-4-4
-

1h
-

,
,

2 Me
5 6
Me +
Neon 4 ,
Cbs
Ome
2
CM3 -
Ht ]

Organic Concepts
?⃝
 Chemistry Organic Concepts Home Work Sheet-5 Solutions

I 13 ✗
"3
ᵈ£K°" n=cu-d%cu •
(Major)
du cuz
→
3
cuz gu with
-

1 conjugated
- - -

•
P
.

"
Br
+
-

cuzcy __
[ 3 benzene singe
-

cuz •
Chinon
≥
Me -13%1%204
'
42504
since there is No -

p
-
y
•
More alkylated

#.

me
or
p
-
c is 4° it will follow SNL

the
Me + me
-

swift ↑e
-
C- cuz -042 Me - C -
CHZ + H2O
the + 1

(highly stable
& µ, , is ,☐gy me

Me simultaneously
alkylated Me d=cn Me
alkene )
- -

-
Ht
" Br H
"° " B
Cuz a
3
Peroxide cHzBr SNZ
.

Hzo 30-+42-04
(Anti M ) -

( 10 )
(Major) -

cry H
•
(Snl )
1. HzS04
+
4- / % •

P
-
C : 3°
cuz cH3 Shift
z ,
_
µ,

(Minos
Organic Concepts
 Me Me
4. 1. Hzpoq 4 56 Me 5 6

Ch -

cuz ch -

cuz
+
g-
Me

¥4 3¥ * 4
-
-
-
-

2
3 ↳
2 .
-

H2O 2
Me
me
cuz (-4-1)
+
Me me
Me +
Chair
Minor (least stable] Minor Gmp)
→
#
a Eto : "
5
cuz
-
cU=C4 -

CUZBV SNZ cuz OEE

cuzcu ch
.

:
-

=
-

10 :
allylic ENYA
( Williamson syn)
Polar Biotic
6 .
Cheng
-
ch =C4 -

cUzBr
Eton : : SNL :
solvolysis .

1° :
allylic
resonance
cnzcn -_Euz cuz _cn=cn ,

Eton _ Eton
~
Ht CU cuz
Chz=cn
-
-
n -1
-
-

◦ Et
•
(EI ) :
conjugated
cnzcu __cH-cnz-0Et cnzd4-cn=cnz 1-

SNL SNL
•
Major as Temp .

is high
Organic Concepts
 Et
Meon Polar Pwtic → solvolysis :
sNʰ/ El : Minor
Et -

& -

Br
-1=2500
Et
Mein
Et " "%

Et Et -
£+0 → Et -1g - ◦ Et

-
Br
-

Et -
H -1 Et -

Et KO"
Étlalc Base : EZ ( Major)
8- Et Br = :
g
- -

Eto " 50°C Et MINOR

There may be a

cHzCn=c[
/
Et
•

#
SNL also as
substrate
Et
with minor
is 3° along
9. Me Eton EL
•
Polar Profic → solvolysis -

A- ↓
Br
Me I. Eton SNL
'
SN
✓
Me
+

✓
•

+
( EI)
←" +
Me
(allylic ) OET

SNL (SNI )
1. Eton
ne ne + me ( EI)
2 -4 +
+ /
.

Eto SNI Products

E:
Major
'T
'
as
is high (
Organic Concepts
 ETEÉ substrate is 2° allylic & Etokt acts as
10 .
(9) H cuz

P It Eton strong base so visualise B- elimination

H Br or Ez reaction to get conjugated diene

cuz : E- 2 : conjugated (highly stable

N+aH5 Substrate is 2° allylic & HS is very
-

(b) cuz
strong nucleophile ( weak base, so visualise
#

Meon
1
45 Br -
SNZ reaction
HS
cuz
SNZ

SH

' •
A'☐ 3
pnez-c-d-uz.ME
shift
Me
_É -

cuz
-
Me

Alds 2? Neo pentyl me

Me
'
SE Rin
cuz Me
+ Me E-cuz
- -
Me g-
1 Me
me

Organic Concepts
2.
(A)
CHzcnzd-hzs-%C4-sd-U-c.tl } -
ch -

cuz
SE Rin dung
ale . KOU : Base : EZ

NB%cl¢
3
but is Pr
'

there no
p
-
Uso

EZ is not
possible .

-9--43 FR
#
visualise EI ( supported by Eton : solvent ) cus substitution
Me
me
-

Me on -ak Me
ne - d -
ciz Me -
c- cuz
-
Me me - c- cuz
-
Me
-
Br
-
I
me
shift +
SNI by SNL
Me the
•
product yield is
cnzz.d-cnz-me-i-ne-d-r.cn -
Me
poor with
at
SNI
25°C
being (EI ) (EI )
major
solvolysis SNL
•

4. Protic : :
:

d-nz +

•
cuz
A
1. Meon SNL .

Ht Chicoine
Énz
2. -

eo
SNL cuz
Organic Concepts Major cuz
:( El]
 Nu
good
-

SNZ Rxn

Chzo Et
1° :
allylic
◦ Et

§
1. Eton

§ cuz
-

cn3
-

I 2
y
(SNL)
-1
CB
.
_

#
solvolysis : SNL cuz

q=cnz (EI)
"
7. 3 •

conjugated
↑
C- c- c- C
43° 1h Eto
-

C=É -
c -
c + c-
{ = C-C
•

major
13 4 13 Ez
(Minor) (Major
BV
Et -
É -
o
-

: weak base so EZ is not

possible .

Etcooie : → Police →
solvolysis can occur ⑤ 1)

E F {
F SNL c- c- c-a + c- = c-a
c- c-a
b-
-

g- Et @ ajorj (EI )
◦
SNL ( Minor
Organic Concepts
 • A similar question we

8. did in
today's class .

Possibility -
I
• here it is SNL .
CEI )
2
3 2
3
"
In
'
1. Ht '

I
4
4/6 A
-
,
2 H shift
2.
-420 ,
H
-5 6

Me
CHZOH Me
#
32-4 : less stable

me
Minor
+

1. H+ @ NL) Me
2. -420 Br
-

Me

Possibility -
II
Br
5 5 6
Br
-

4 +
6 1- ,
4
Cuz
/
•
-

12
.
-
" - 2 3
3 _
-

2
me •
42-4 Me

Chagos
me •
More
Stable

Organic Concepts
9. HBR
Me Me Me

+ + 3-2-4 : less stable .

4×-4 : More stable • 4- Shift

Si

Me Me

#
Br (Major pg
(Minor

10 • • 168¥ 1804
1
.

30

20 -4201°
• 3° alcohol will protonated .
as it
stable carbocation
give more
Contd
.

. . . . .

Organic Concepts
160%9 % +
¥4
/
°
(Nu)

3 5

-4201° 4

↑
-

is 5018 (-4-1)
# 0 +
5 1

a
-4-1
4
?
2

%
SNL ( 1 : MINOR)
( major) @ Tis NOT 1702 )

Organic Concepts
 Chemistry Organic Concepts Home Work Sheet-6
1- .

2.

(Path -
I )

Organic Concepts
3. Identify the products .

4.

Organic Concepts
 & Products
5. Identify Major minor .

1 H
.

ate 'K°H Minor

Br Major +

Ph
H Me
2-
MezcENÉ
Br
#

the
Mezcal,
Br
3. EÉONA
0
Eton #
,

Me

4. 5h
Me OH #
,

F
Me
5-
Him H
alc KOA
,

.
""

Br
""
"'

É= Me

H Organic Concepts
 & Products
6. Identify Major Minor .

Ht
1. /

OH

04
2. Ht
L

3. Hzpocpcc]

OH

4 .

cuz
-

cuz
- É -
n
0-4
'
on

§
5.
0-4
an
cuz n
- - -

'
on

Organic Concepts