Organic Chemistry – 22CT104

Module 1 -T2 Extension Questions

Part – A Questions

1. a) Predict the electron geometry and molecular geometry of molecule with steric number 7 with a
center atom that is only bonded to 5 other atoms and 2 lone pairs of electrons.

b) Explain how carbon atom in CH4 achieve configuration similar to Neon (Ne) element?

c) How will you explain the 2 peaks with 1:3 ratio observed in photo-ionization spectrum of CH4
molecule?
d) How do you differentiate hybridized orbitals from molecular orbitals and atomic orbitals.

e) Predict the hybridization of C and N centers in given amino acids.

2. a) Use VFSTR theory to determine the molecular geometry of each of the following and also
determine the relative bond angles based on lp-lp, bp-lp, bp-bp repulsions.

1 SNF3 4 NO3-
2 XeO3 5 ClF5
3 I3 - 6 SF4

b) Sketch the most likely structure of PCl3Br2 and explain your reasoning for the placement of
the axial and equatorial ligands.

c) In PCl3(CF3)2, would you expect the CF3 groups to occupy the same positions as the Br
atoms? Explain your answer.

d) In PCl5, would you expect the axial and equatorial bond lengths to be same of different? If
different, which would be longer? Explain your answer.

e) Is the axial P-F bond length longer in PF2Cl3 or PF2Br3? Explain your answer.
3. Pyridine is a basic heterocyclic compound with the chemical formula C5H5N. It is structurally
related to benzene, with one methine group (=CH-) replaced by a nitrogen atom. It is used to
make many different products such as medicines, vitamins, food flavorings, paints, dyes,
rubber products, adhesives, insecticides, and herbicides.

a) Draw the orbital diagrams to show the orbitals of the C and N atoms involved in the σ and
π bonding in pyridine.

b) How many bonding and antibonding molecular orbitals are present in Benzene and
Pyridine? Draw the molecular orbital diagram to explain this answer.

c) Based on the answer (b) explain how many delocalized electrons are present in benzene and
pyridine molecules.
4. a) Draw the rearranged carbocations and discuss their comparative stability.

b) Sketch the reaction coordinate versus energy diagram of the following unimolecular
reaction. Reactant 1 is solvated to carbocation 2. Then carbocation 2 rearranges to carbocation
3. Finally, the solvent reacts with carbocation 3 to form product 4.
c) Predict both major and minor products for the following reactions.

c) Predict the product(s) obtained from addition of singlet and triplet dichlorocarbene to each
of the following compounds and indicate whether they are mesocompounds or pairs of
stereoisomers.
5. a) Mark all the chirality centers in the “Lovastatin” bromine derivative shown below with an
asterisk (*). How many chirality centers are present?

b) Draw the structures of all possible isomers of dichloro-cyclo-butane and determine their
symmetry elements. Assume that the cyclo-butane ring is planar. Indicate which isomers are
chiral.
c) Identify the given compounds are enantiomer’s or diastereomer’s. Assign the R or S
configuration to each stereogenic carbon center.
6. a) Determine the conformation of the following compound and convert the representation into
a Fischer projection formula.

b) Classify the following radicals as primary, secondary, tertiary, benzylic, or allylic.

c) Identify the possible reaction intermediates and products in the below given reaction
scheme.
7. a) Arrange the following carbanions in order of stability.

b) Assign the configuration of the stereogenic units in following amino acids.

c) Identify the possible reaction intermediates and products in the below given reaction
scheme.
8. a) Use VFSTR theory to determine the molecular geometry of each of the following and also
determine the relative bond angles based on lp-lp, bp-lp, bp-bp repulsions.
1 SNF3 4 SO3-
2 XeO3 5 ClF5
3 I3 - 6 SF4
b) Determine the conformation of the following compound and convert the representation into
a Fischer projection formula.

c) Predict both major and minor products for the following reactions.
9. a) Draw the rearranged carbocations and discuss their comparative stability.

b) Identify the given compounds are enantiomer’s or diastereomer’s. Assign the R or S

configuration to each stereogenic carbon center.

c) Predict the product(s) obtained from addition of singlet and triplet dichlorocarbene to each
of the following compounds and indicate whether they are mesocompounds or pairs of
stereoisomers.
10. a) Draw and specify as R and S enantiomers for the following compounds.
i) 3-Chloro-4-methyl-1-pentene
ii) HOOCCH2CHOHCOOH
iii) C6H5CH(CH3)NH2
iv) C6H5CHOHCOOH
v) C6H5CH(NH2)COOH
b) Assign the configuration of the stereogenic units in “Ataprost”, an inhibitor of platelet
aggregation.

c) Construct the MO energy level diagram of Benzene and represent the number of nodes in
each linear combination and also identify the HOMO-LUMO levels.
 Part – B Questions

1. a) Predict the possible products in the following reactions and justify your answer with suitable
mechanism.

b) Assign the configuration of the stereogenic units in “Remdesivir” an antiviral medication

to treat moderate COVID-19.

2. a) Reaction of an Alkene with hydrogen bromide results in formation of alkyl halide.

i. Complete the products (major vs. minor) obtained in the above reaction.
ii. Construct the various conformers of the minor product obtained.
iii. Justify the stability of each conformational isomer.
b) Represent the pi-bonding modes in 1,3-butadiene & 1,3,5-haxatriene by using MO energy
level diagram. Also represent the HOMO and LUMO levels in each case.