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REACTIVE INTERMEDIATES CARBENE AND NITRENE

Assignment- Week 1
TYPE OF QUESTION: MCQ/MSQ
Number of questions: 15 Total mark: 15 X 1 = 15
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QUESTION 1:
Correct electronic configuration for singlet carbene is

a.
H

H
b.
H

H
c.
H

H
d.
H

Correct Answer: a

Detailed Solution: Singlet carbene has no unpaired electron; both the electrons are in a sp2
hybrid orbital. Thus a is correct answer

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QUESTION 2:
Which one among the following is ESR active?
a. Triplet carbene
b. Singlet carbene
c. Both of them
d. None
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Correct Answer: a

Detailed Solution: Triplet carbene has two unpaired electrons, thus has a net magnetic moment
and its ESR active

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QUESTION 3:
Which one of these carbene is most electrophilic in nature?
a.
C(OMe)2
b.
CH2
c.
CCl2
d.
OMe
C
F

Correct Answer: c

Detailed Solution: Option c is the most electrophilic in nature, whereas option d is ambiphilic in
nature, see leacture

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QUESTION 4:
O O
Me S
N base
P
N
O

Here the product P is

a.
Me
N
N
O
b.
H2C N2

c.
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O O
Me S
N

d.
N O
N
H

Correct Answer: b

Detailed Solution:
OH OH
H
O O H
Me S H N
N
N CH2N2
N OH
O
H+
PTSA

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QUESTION 5:
Among the following which will NOT provide :CCl 2

a.
CHCl3

b.
CH2Cl2

c.
CCl3COONa

d.
CCl2F2

Correct Answer: b,d

Detailed Solution: See Carbene generation part from the lecture

CHCl 3 under basic condition (NaOH/KOH) and CCl 3 COONa under heat will produce :CCl 2
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QUESTION 6:
O

OH CH2N2 P

Here the product P is

a.
O

b.
O

c.
O

d.
O

N2

Correct Answer: c

Detailed Solution:
O O
-N2 O
R OH R O H3C N2
CH2 R O
N2

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QUESTION 7:
O
CH2N2
M N2
R

Here M is

a.
O

R OH

b.
O

R H

c.
O

R NH2

d.
O

R Cl

Correct Answer: d

Detailed Solution:
O O O
N
R Cl N N N
R R
H H
CH2 H
N2 CH2
N2

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QUESTION 8:
Total number of valence electron in carbene is.

a. 2
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b. 6
c. 8
d. 4

Correct Answer: b

Detailed Solution: See lecture

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QUESTION 9:
O
+ NaOMe
Ph Ph TsNHNH2 M
heat

Here the product M is

a.
NH2

Ph Ph
b.

Ph Ph

c.
OH

Ph Ph
d.
H
N
N Ts

Ph Ph

Correct Answer: b

Detailed Solution:
H
O TsNHNH2 N
N Ts NaOMe, Heat
Ph Ph Ph Ph Same as Bamf ord Ph Ph
Stevens

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QUESTION 10:
H 1. BuLi (-115 °C)
R Br
M
then ( -90 °C)
Br

Here M is

a.
RCH2Br

b.
R Br
c.
R H
d.
Br Br

Correct Answer: c

Detailed Solution:
H 1. BuLi (-115 °C) H H
R Br R Br R Br R H
Br Trans lithiation ( -90 °C) Li
Li α−elemination
n
Li Bu

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QUESTION 11:
hν CF3
M
R

Here the starting material M is

a.
N N
CF3

R ‘
b.
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NHTs
N

CF3

R
c.
O

CF3

R
d.
Cl Cl
CF3

Correct Answer: a

Detailed Solution:

N N N N

CF3 hν CF3 CF3

R R R
N2

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QUESTION 12:
O H
N NaOMe P
+ N Ts
R H Rh2(OAc)4

Here the major product P is..

a.
O
CH3
R

b.
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c.
O
R
CH3

d.
O

Correct Answer: c

Detailed Solution:
O R
H Base Rh(II) O
N N2 Rh
N Ts -Rh(II)
R

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QUESTION 13:
In the given reaction, the following products M & N are formed. Here compound N is

O O O O
TsN3, Et3N
N
O O
N2
M

a.
O O
S
NH2

b.
O O
S
OH

c.
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O O
S
N3

d.
O O

N3

Correct Answer: a

Detailed Solution:

Look for the mechanism of Regitz-diazo transfer reaction.

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QUESTION 14:
Among the following carbenes, most stable carbene is

a.
O O

O O

b.
Cl Cl
C

c.
O O
C

d.

N N

Correct Answer: d

Detailed Solution:

See lecture on carbene stability

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QUESTION 15:
Which of these following reaction(s) do(es) not proceed through a carbene intermediate

a. Reimer–Tiemann reaction
b. Wolff rearrangement
c. Simmons–Smith reaction
d. Curtius Rearrangement

Correct Answer: d

Detailed Solution: Curtius Rearrangement goes through nitrene rearranging into isocyanate.

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