BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE, PILANI - HYDERABAD CAMPUS

1st Semester, 2021-22

CHEM F212: Organic Chemistry I Midsemester Exam Closed Book
Max. Marks: 60 Time: 90 minutes Date: 18th Oct, 2021
Instructions: Write your name and ID. Answer all four questions. Write on a white page clearly
using pen only with a sequential page number, take a snap, make a pdf with your name XXX.pdf
and upload the file in Mettl. Please send the same pdf file to manab@hyderabad.bits-pilani.ac.in
within the given time. Write in short.
Q1. (a) Identify the appropriate HOMO and LUMO orbitals involved in the following reactions.
Write the attack with properly curved arrows (Identification of products are not necessary).5M

(b) Why is the side on the overlap between py and pz orbitals are not strong? 2M
(c) Explain why nucleophiles and electrophiles would prefer to have equal energy during the
reactions? Explain with an MO diagram and a single sentence. 2M
(d) Protonated form of Ph-CH2-O-Me reacts with cyanide nucleophile. Find all possible products.
3M

(e) What is reason behind to have a planar structure for a carbocation when formed from alkyl
chloride? 3M
Q2. (a) Mention the intermediate for this reaction and state the
preferred geometry. No structure is needed. 2M
(b) The positive charge on the CH3CH2+ is stabilized by hyperconjugation. How can MO theory
explain it? 3M
(c) If we want to generate a carbocation from the following compound to characterize
through NMR, specify two necessary measures required for the same. 2M
(d) Find the best route for reaction (i). Identify A-C as a major product from the following
reactions (no mechanism is required). 2.5+3=5.5M

(e) Compare the reaction rate between A and B when treated with a methoxide ion with an
explanation. 2.5M

Q3. (a) Two chemists argue on this reaction mechanism, either E2 or E1. How can you establish
the reaction mechanism (give support for both individual possibilities) without evidence of
forming other side products? 4M
(b) The generation of a carbocation from the reaction between Me 2C=CH2 with HCl is
endothermic. How will the transition look like (give the structure)? 3M
(c) Find A and B for reaction (i). Find C and D by mentioning the kinetically and
thermodynamically controlled products. What will be the nature of slope [reaction constant (ρ)]
for both these reactions (i) and (ii). Find two major mono brominated products (E+F) from
reaction (iii). 2.5 + 3.5 +2 =8M

Q4. (a) How can benzene be converted to C6H5D? Find the stable products formed when 1-(tert-
butyl)-4-methylbenzene is treated with H+. 3M
(b) On the basis of the given data, how much faster m-methoxybenzylchloride will hydrolyze
compared to p-cyanobenzylchloride. σp(CN)= 0.67 ; σm (OMe) = 0.11 and ρ = -1.31. 3M
(c) Comment on the substitution effect (X) for reactions (i) and (ii). What will be the nature of
slope [reaction constant (ρ)] for both these reactions. 4M

(d) Find out the possible products. Comment on the stereochemistry

of the products to confirm the type of carbene. How one can make
this carbene without using any toxic diazo compounds. 1+2+2=5M
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