Birla Institute of Technology and Science, Pilani - K. K.

Birla Goa Campus

Comprehensive Examination, CHEM F337, Green Chemistry and Catalysis,
1st Semester, 2021-2022, Date: 27.12.21
Max. Marks: 80, Time: 3 Hours
Part A
Note : Question Paper consists of two parts, Part A & Part B.
Part A is for 40 marks & is closed book. Answer all questions and all parts of each question together.
Maximum duration for this part is 1 hr 30 min. Part B is for 40 marks & is open book. Part B will be given
only after Part A answer sheet is submitted. If Part A is complete before 90 min, you can submit it & start
answering Part-B. Total duration for Part A and Part B is 3 hrs.

1. A) Match the name of the inventor with corresponding Reagent/catalyst/process. B) Match the table with
corresponding name reaction for C-C coupling reactions. 2+3
A) Name Reagent/catalyst B) Substrate Inventor’s name
/process Ar-ZnX Kumada
Jorgensen [RhCOD(PPh3)2]+ Ar-B(OR)2 Stille
Schrock- Caprolactum Ar-SiR Negishi
3
Osborn
Ar-MgX Hiyama
Takasago Menthol
Ar-H Suzuki
Rhodia Organocatalysis
Ar-SnR3 Murai

2. The following molecule can be selectively hydrogenated using different catalyst like a) Pd/C, b) Rh(PPh3)3Cl, c)
[Ir(COD)PCy3Py]+PF6- to yield different products as mentioned below. Match them with the following reactions.
1x3=3
O

O
B O

3. Predict the products of the following reductive ozonolysis reaction. 1x2=2

O

1. O3
? + ? + HCHO
2. CH3SCH3

4. Predict A and B of the following reaction. 2

H2, Pd/C CO
O A B
PdCl2, PPh3

5. A) Describe transfer hydrogenation with appropriate example. 2

B) The ratio of preferred product for case B is increased up to 999:1 by putting a methyl group with the alcoholic –OH
group. Suggest an appropriate reason for the improved selectivity. 3
P.T.O.
 A B
5. Suggest a plausible mechanistic pathway for the formation of following products showing the intermediates. 3

6. (A) What is organocatalysis? Mention four points to explain why proline is the best organocatalyst. 3
(B) Jorgensen catalyst (A) is a well-known, commercially available organocatalyst useful for many
transformations. It can be formed from L-proline and B is an intermediate in the synthetic scheme.
(a) Suggest appropriate reagents and intermediate steps for the conversion L-proline to B. (b) Explain why B
is not a suitable catalyst for the following reaction. (c) Mechanistically explain how Jorgensen’s catalyst
predominantly produces S-isomer in the following reaction. 6
F3C F3C
EtOOC EtOOC
N catalyst A NH O CF3
CHO + CF3
N N N CF3 CF3
COOEt solvent EtOOC H N
(S) H H
TMSO HO
A CF3 B CF3
7. (A) Explain why C-H bond activation is a very difficult task to achieve. 2
(B) What is the full form of DG. Why a DG is essential for most of the C-H bond activation? Give an
appropriate example explaining the role of DG. 3
(C) What is the full form of CDC. Mention any one “green” method of CDC and explain why you think this
is an example of green approach. 1+2=3
(D) Matt Gaunt observed a unusual meta selectivity for the following C–H Arylation reaction.
Mechanistically explain why and how meta-selectivity is favoured. 3

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