BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE, PILANI - HYDERABAD CAMPUS

1st Semester, 2017-2018

CHEM F212: Organic Chemistry I Midsem Test (Regular) Closed Book
Max. Marks: 50 Time: 60 minutes Date: 10th Sep, 2011
Note: There are FOUR questions in all. Ensure that both sides of the paper are printed. Start answering each
question on a fresh page and answer all parts of the question together. Pencil should not be used.

1. (a) Both the alcohols A and B can form carbocation in the presence of an acid. Compare the
feasibility of carbocation formation from these two alcohols. Is Cyclopropylhalide a good
substrate for nucleophilic substitution reactions? How can one detect a carbocation
experimentally? 2+2+1 =5

(b) Br2 can react with a nucleophile but C2H6 cannot. Explain in short using MO theory. 3

(c) Can a nucleophile react in this fashion as shown here? Justify your
answer. 2

(d) Compare the stability of these free radicals with justification. 2

2. (a) Why singlet carbene bond angle (RCR) is usually smaller than triplet carbene? 2

(b) Both RCHCl2 and RCH2Cl can form carbenes. What difference can be found in forming carbenes from these
two halides? 2

(c) Find the products possible from this reaction and comment on the
stereospecificity. 1+ 3

(d) Mention a recent application of carbene? 1

(e) Find A to F as suggested. 2+1+1+1=5

For reaction (iii), how do you study the reaction intermediate and confirm the product formation 2

3. (i) Find A (with proper stereochemistry) and what product(s) can be expected from A from the next reaction as
shown here. Mention one practical advantage and disadvantage of OsO4. 4
(ii) Find the products coming out of these two reactions (no mechanism is required to show) 3

(iii) Find the most and least acidic phenol? Justify in one line. 2

(iv) Suggest a possible route of synthesis for the following compound using Grignard
reagents. (mechanism is not required). Just write the compounds to be used. 2

4. (i) What is the basic difference between primary and secondary kinetic isotope effect? Mention two factors that
affect the secondary kinetic isotope effect. 2

(ii) Mention two reagents (of different type) that are generally used to bring inorganic salts to be active in reacting
with organic compounds. 2

(iii) Predict the sign of reaction constant for these two reactions. Will there be any difference in values? If so, which
one will be higher and state the reason. 3

(iv) Give an example for each (a) ρ > -6.0 (b) ρ = +ive. 1

(v) Give a mechanism for the following reaction used on the concept of nucleophilic aromatic substitution reaction.
2

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