NPTEL Course on Cycloaddi4on

Instructor: Prof. Krishna P Kaliappan

Department of Chemistry, IIT Bombay
(Teaching Assistant: Animesh Sau)
Assignment 0

1. The arrow used in a pericyclic reaction refers to-

(i) Nucleophilic attack
(ii) Electrophilic attack
(iii)Peripheral flow of electrons
(iv) Radical coupling

Answer:
(iii) Peripheral flow of electrons

2. Identify the major product in the following Diels-Alder reaction.

O
Δ
A

O O

(i) (ii)

O O

(iii) (iv)

Answer:
O

(ii)
3. Identify the major cycloaddition adduct from the following reaction.

H Δ
P

OHC
O

(i) CHO (ii) CHO

O O CHO OHC CHO

O
(iii) (iv) (v)

Answer:

O CHO

(iv)

4. Which one of the following is the correct combination of orbital energy of butadiene
and ethene?

(i) EHOMO (butadiene) > EHOMO (ethene) and ELUMO (butadiene) > ELUMO (ethene)
(ii) EHOMO (butadiene) > EHOMO (ethene) and ELUMO (butadiene) < ELUMO (ethene)
(iii) EHOMO (butadiene) < EHOMO (ethene) and ELUMO (butadiene) < ELUMO (ethene)
(iv) EHOMO (butadiene) < EHOMO (ethene) and ELUMO (butadiene) > ELUMO (ethene)

Answer:
(ii) EHOMO (butadiene) > EHOMO (ethene) and ELUMO (butadiene) < ELUMO (ethene)

5. Identify the structures of A and B from the following sequence of reactions.

O
CO2Me
H2, Pd/C Δ
A B
CO2Me
 O
CO2Me
O
A= B=
(i) CO2Me

O
CO2Me MeO2C
A= B= O
(ii) CO2Me MeO2C

O
CO2Me MeO2C
A= B= O

(iii) CO2Me MeO2C

O
CO2Me
A= B= O

(iv) CO2Me

Answer:
O
CO2Me MeO2C
A= B= O
(ii) CO2Me MeO2C

6. Identify the correct combination of the products from the following

reaction-

N
Ph C
O
R NO2 Products

(i) R N O PhNH2 CO2

R H
N O N OH
Ph
(ii) O
 H
N OH
R N O Ph
(iii) O

R
PhNH2 CO2
(iv) N O

Answer:
(i) R N O PhNH2 CO2

7. Which of the following condition will not deliver benzyne?

F Mg

(i) Br

TBS TBAF

N2
(ii)

N Δ
N
S
(iii) O2

(iv)

Answer:
Δ

(iv)

8. The major products formed in the following reaction sequence are-

i. CBr4, PPh3 PhN3

CHO P Q
CuSO4
ii. excess nBuLi sodium ascorbate
 Br N3
and Q=
(i) P= Br N3

P= and Q=
Br N3
(ii)

Q= N
P= C and N
N
(iii) Ph

P= N
and Q= N
N
(iv) Ph

Answer:

P= N
and Q= N
N
(iv) Ph

9. Identify the major products in the following reaction sequence -

O
Δ
O
P Q

H O

O
P= Q=
H O
(i)

H O

O
P= Q=
H O
(ii)
 H O

Q= O
P=
H O
(iii)

H O

P= Q= O

H O
(iv)

Answer:
H O

Q= O
P=
H O
(iii).