Department of Chemistry

CML 101: Organic Chemistry: Tutorial 3

Instructor: Dr. Nidhi Jain (Room: MS 727)

Q1. Which of the following reactions will show kinetic hydrogen isotope effect? Explain with
the help of mechanism and identify the RDS. Give the product formed in reaction (ii) and
draw the labeled energy profile diagram.

(i) HNO3
H2SO4 (Conc)

Br
(ii) Me CHMe2 NaOEt
EtOH, Heat

Q2. Draw the structures of A, B, and C in the following scheme, and suggest a reason for the
difference in the relative rates.

(i) KI, aq. THF, H+

A + B (two iodide products, fast reaction)
OH

(ii)
KI, aq. THF, H+
C (one product, slow reaction)
OH

Q3. Arrange the following compounds in increasing order of their reactivity.

O X X X X
(i) O
O (rate of solvolysis)

I II III IV

CH3 CD3 CH3 CH3 CD3

(ii) CH3C Cl CD3C F CH3C F CH3C Br CH3C F (E2)
CH3 CD3 CH3 CH3 CD3
I II III IV V
Q4. Identify the major product in the following reactions with correct stereochemistry
wherever applicable.
Et
1. Cl2, H2O b)
a) CH3CH2CH2CH=CH2 Br H NaOEt
2. NaH
Me H EtOH, Heat
OCOCH3
OTs Ph
c) AcOH OH
KOAc d) H3PO4
Cl 120 oC

e) KOCEt3 Cl
120 oC f) CH3CH2OH

Q5. Which one of the compounds (I or II) reacts with Cl- to give (III)? Give the mechanism of
its formation.
OCH3 OCH3 Cl

C C C
O Cl O Cl O OCH3
I II III

Q6. On attempted E2 reaction, (I) reacted much faster than (II). Write the product of the reaction
in each case and explain the reason.
CH3 CH3

D D
H CH3 H CH3
Br Br
I II

Q7. For the following transformation, intermediate azirene was isolated. With the help of
intermediate structure, propose a suitable mechanism for this reaction.

NH2
Et Me Et
Me NaOEt Et
Me
N then H2O N
OTs O
azirene