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This Study Resource Was: Department of Chemistry, IIT Bombay

The document is an exam for an organic chemistry course that contains 11 questions testing students' knowledge of organic chemistry concepts. The questions cover topics like identifying constitutional and stereoisomers, orbital interactions in rearrangements, drawing reaction mechanisms using curved arrows, assigning stereochemistry and determining major products, assigning R/S configurations, drawing stable conformations and identifying symmetry elements, comparing stability of ionized forms and dipole moments of molecules, and matching reaction energies to transition states. Students are instructed to show their work and use blue or black pen, with answers in pencil not being graded.

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Sandipan Saha
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240 views2 pages

This Study Resource Was: Department of Chemistry, IIT Bombay

The document is an exam for an organic chemistry course that contains 11 questions testing students' knowledge of organic chemistry concepts. The questions cover topics like identifying constitutional and stereoisomers, orbital interactions in rearrangements, drawing reaction mechanisms using curved arrows, assigning stereochemistry and determining major products, assigning R/S configurations, drawing stable conformations and identifying symmetry elements, comparing stability of ionized forms and dipole moments of molecules, and matching reaction energies to transition states. Students are instructed to show their work and use blue or black pen, with answers in pencil not being graded.

Uploaded by

Sandipan Saha
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Department of Chemistry, IIT Bombay

CH 105:Organic Chemistry
End-Semester Examination
Marks: 25 Time: 2 hours September 13, 2017

All answers must be written using blue/blackpen. Answers written with pencil will not be corrected.

1. Identify the following pairs as “Identical / Enantiomers / Diastereomers / Constitutional isomers”.


(2 marks)
a. b.

2. Identify the orbital interactions involved in the following rearrangement. (1 marks)

m
er as
co
eH w
3. Identify the structure of the productofthe following reaction. Explain its formation with the help of

o.
arrow-pushing mechanism. (3 marks)

rs e
ou urc
o

4. Provide an arrow-pushing mechanism for the formation of the product in the following reaction.
aC s

(3 marks)
vi y re
ed d
ar stu

5. In the following reaction: A. Write the conformation of the starting compound. B. Identify the orbital
interactions involved for ‘*’arrow. C. Identify the stereochemistry and the structure of the major product.
(3 marks)
sh is
Th

6. Assign the absolute configurations (R/S) for the following molecules. (2 marks)
a) b)

https://www.coursehero.com/file/44889894/End-Sem-2017pdf/ 1
7. Write the most stable conformations of the following molecules. Identify and pictorially show the
symmetry elements present inthatconformer. (4 marks)
a) b)

8. Which of the following bromides will give more stable ionized form in a polar medium such as acetic
acid? (1 mark)

9. Which of the following ketones will have higher dipole moment? (1 mark)

m
er as
co
eH w
o.
10. Based on the analysis of the highest occupied molecular orbital (HOMO) and the lowest unoccupied
rs e
molecular orbital (LUMO) (show picture), identify whether following reaction will take place. Your
ou urc
answer should be based on the orbital interactions. (3 marks)
o
aC s
vi y re

11. Match the structures in Column P with the ‘A values’ in Column Q. (2 marks)

  Column P    Column Q (kcal/mol)
ed d

1.  a.  0.8 


 
ar stu

2.  b.  1.8 


 
sh is

3.  c.  2.9 


Th

4.  d.  4.0 


 

https://www.coursehero.com/file/44889894/End-Sem-2017pdf/ 2

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