Organic Concepts

Homework

Solutions to HomeWork-Sheet-2

HomeWork-Sheet-3
Based on Nucleophilic Substitution
-
 Chemistry Organic Concepts Home Work Sheet-2
I.

1°
20
↓
faster
-

is better leaving
as I
group
.

faster
( tn Snf path steric hindrance is key factor)
,
#

2.

(i ]
10 10 20
c- { ¥3s (SNZ)
{
c- c- c-c- Bv > c- c- Br Br >
> c-c-
g
- -

c d
É Bv >
( SNY
c- c-c- Br >
-

{ ≥
c- c- c- c- Br C Br
-

§
c-
- -

'
c
10 20 2%1-(22-4) 1%1-(1×-4)
(Ii ) C6H5CHzBr > CGHS
GH Br >
20
3°
Colts
CGH-s-q-cco-H-D-BRC.SN }
-
CH Brr 7)
- -

461-15
(611-5 £43 Colts
GHS -4 -
Br
> Colts GH Br > Colts GH Br > ↳ HsCHzBr (SNL)
- -
-
-

Colts Colts cuz

Organic Concepts
3 .

10 20
20

3°
faster
faster

pic
'
observe steric hindrance at
#

4.
focus on stability of carbocation

3° 20 20 10

5 .

better
_

I :
leaving group Me -
CI : has least steric hindrance

Organic Concepts
6.

CN-C-C-c-E.BR C- c-c-c- c + Br
-

[good Nu ) 1° → SNZ
SNZ leaving group
↑
NC - - - -
C - - - -
Br
3Ds / "
H
slow C-C-C
#

7.

( is 1- Bromo pentane > 2- Bromo

pentane 2- Bromo -
2-
methyl butane
steric hindrance
Br Br
Lii) c - c -
c -
c -
Br > c- c- E- c > d- C
' c- c-
c d a
'

8. Identify the stronger nucleophile in each pair .

(il) 54 & En ICI cis DMSO

-

C) & in Hzo in Meon Liii,

-
- -

Br C1 Cl

Civ ) Hzs & 420 (V) PHE & Phon (Vi ) Pkg & NH
}
Organic Concepts
9. In which of the following pair of reactions ; SNZ path is
faster
.

Meal DMSO
I. (A)
-

Meo (B)
-

Br + ; Br + Meo

Cl 9
II. (A) -1 Me Coo ; (B) +
Naottaq
Nat Mesina
-

III. (A) I + Mes

, (3) +
±

#
I : Dmso ;
Aprotic solvent favours SNZ path
I/# : Better
nucleophile increases rate of SNZ path
10 .

Organic Concepts
 H
"
Iii?
I 1
DM / .
ti
C- Br

Ak ☐ Et Mein
Et

✓
is poetic solvent
◦
MEOH polar
◦ Meon is a weak Nucleophile ,

it will follow Sn
'
Mechanism .

H H

1 I
'D
DX / C -
ome + Meo -
C "
'

• • Et

Et

Racemic Product

P block C̲ i ̲r ̲c̲l ̲e̲

iii )
me•£•B Nazi
E- TOH
me - MCN

cni is
( Inversion Product)
strong
◦
a

Nucleophile
°
It will follow SNZ

~mq¥
"

)~•==µ~
iv I

me

is
-

strong
SH
Nucleophile
•
a

◦
will follow spy 2 -

P block C̲ i ̲r ̲c̲l ̲e̲

 Et ◦ Et

Fr
◦

D- - % + -

Eton is Photic solvent

°
polar
◦
C- tote is weak Nui , will follow SN
)

Mechanism

◦☒Eᵗ
Br

A- → É← ~-
+

OET

( Racemic Product )

P block C̲ i ̲r ̲c̲l ̲e̲

 Ph
Ph

Hmla
•
me
É
me
✗

◦
H2O is polar protic Solvent .

Ph Ph
°
It
follow Snl path " /
"
" 1/-5,1 HÉ _ "" H
⑧
+

Ba
-
,

me
Me

( Racemic

product ) ph
~

-1
Ph

HM
2g -
OH
+ Ho
•
' "' "

P blockme
me

C̲ i ̲r ̲c̲l ̲e̲
#

Distereomers

Organic Concepts
 ⊕

p•Bo
ix ) -

=_
me
✓É-m ! Hao

1 , 2

shift
-

◦
H2O is a
polar psotic Solvent

H2O is weak Nucleophile

⊕me
◦

◦
It will
follow SN '

HÉO
.

me

OH
P block C̲ i ̲r ̲c̲l ̲e̲
 Ei⇐%"iµ→
"

me
me

Nj is Nucleophile follow SNZ

strong
◦
,

Observe CF 3503-0 ( Triflate ion ) is

good
: a

leaving group
.

P block C̲ i ̲r ̲c̲l ̲e̲

 Chemistry Organic Concepts Home Work Sheet-3

I. Identify the product & path of reaction . denlify Pain .

1 H2O
.

Cuz -
O -

GH
-
Br t

CH3

2.
Mez-i-N-CHz.CI 1- Me OH
#

3 .
Cuz -
§ -

CHZCI 1- H2O

4 .

Cuz
-
É -

Cuza + KCN
Eton

5. -

GH
-

cuz + CHzcoo-wac43.com
Br
Eton
6. + Ken
GH cuz
-
-

Br

7.
-

GH
-
CH
'
-

cuz
1-
Koltaq
Br
cuz
Organic Concepts
 Maths
-

8 CH
Chzcl
Cuz -4
-
=
.
,

cuz
H2O
Cuz -4 Ch
Chzct
-
=
9 .
>

cuz
443 NaN }
10
Cuz g cuz cuz
- -
.

B. ✓

II.
a)
Visualise the reaction mechanism of Finkelstein reaction .

b) Why it is a Reversible Reaction ?

c) How can one force the reaction to

go in forward direction
III. Eton
me me

n BV NaN3

comment
upon stereochemistry of product also .

Organic Concepts
 comment
upon stereochemistry of product also .

II the H Eton

CH3C05Na→
H By >

I
# Koltaq .

Cl H

H 5 Me

VI Oltaq .

H H

Cl 5 Me

VII.
aon

Br
aq .

¢-14)
Organic Concepts
 %.
*oBr
+ NASH >

NaOH

420

II. Brz NaOH Meng Br H2O

# > , >
cone
H2O THE

Ck -04
I. > >
cone
H2O

Organic Concepts