1.

(a) From the following reaction, you can find two major compounds A and B (one of
them is non-brominated). Identify A and B with molecular structure.

Q. Choose the compound in each of the following pairs that reacts faster with sodium methoxide
in methanol at 50°C:

Q. Identify C and D:

Q.

Q. Estimate the pKa values at 25 oC of 3,4,5-trichlorophenol when the pKa (phenol) = 9.92 , σCl
(p)= 0.23 ; σCl (m)= 0.37 and ρ = 2.25.

Q Explain the difference between these Hammett ρ values by mechanisms for the two reactions.
In both cases the ring marked with the substituent X is varied. W hen R= H ρ = -0.3 but when R=
Ph, ρ = -5.1
 Q. on the basis of the given data how much faster p-bromobenzylchloride will hydrolyze
compared to p-nitrobenzylchloride. σp(Br)= 0.26 ; σp (NO2) = 0.81 and ρ = -1.31

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?

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

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

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

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

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

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

(d) Mention a recent application of carbene?

(e) Find A to F as suggested.

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