ORGANIC CHEMISTRY

EASY

1. Which of the following compounds is the MOST reactive towards CH 3CH2Cl, FeCl3 ? (10 Seconds)

A. B. C. D.

Answer: C

2. Which of the following is the MOST susceptible towards a nucleophile attack? (10 Seconds)

A. B. C. D.

Answer: A

3. Which of the following statements concerning the Friedel-Craft’s alkylation is correct? (15 Seconds)
I. The reactions is classified as an electrophilic aromatic substitution
II. Both aryl and alkyl halides may be used to initiate the reaction with the aromatic compound.
III. It involves the use of a Lewis Acid
IV. It involves the use of a Lewis Base

A. I and IV only B. I , II and IV C. I and III only D. I, II and III

Answer: C

4. For the given reaction below . Give the IUPAC Name of the major product. (15 Seconds)

Answer: Cyclohexa-1,4-diene or 1,4-Cyclohexadiene

5. For the given reaction below. Give the IUPAC Name of the major product . (15 Seconds)

Answer: Cyclopentanone

6. Draw the structure of m-chloroperoxybenzoic acid. (15 seconds)

Answer:
7. Give the complete name of this reagent which is commonly used in oxidation reactions of primary and secondary
alcohols. (15 seconds)

Answer: Pyridinium chlorochromate

8. Histamine is responsible for many physiological responses and is known to mediate the onset of allergic reactions.
Arrange the following N atoms in histamine according to increasing basicity. (10 seconds)

Answer: A < B < C

9. How many isoprene units are there in α-pinene shown below?

Answer: 2

Isoprene is also known as 2-methyl-1,3-butadiene which consists of 5 carbon atoms in its skeletal unit. The color coding
below indicates the location of the two isoprene units in α-pinene

10. Aeruginosin 298-A is a protease inhibitor isolated from blue-green algae. Part of a recent synthesis of Aeroginosin
298-A is outlined below.

What do you call the reaction happened in the above scheme?

Answer: Birch reduction

AVERAGE
1. Given the following reaction. Draw the structure of the major product. (60 Seconds)

Answer:

2. Given the following reaction. Give the IUPAC Name of the major product. (60 Seconds)

Answer: 2-Butanone

3. Given the following reaction. Give the IUPAC name of the major product . (60 Seconds)

Answer: 2,3,4,5- Tetraiodopyrrole

4. Give the IUPAC name of the alkyl halide product for the following reaction. (60 Seconds)

Answer: 2-Bromo-2-Methylpropane

5. Give the IUPAC Name of the major product for the following reaction. (45 Seconds)

Answer: 3-Ethyl-5-Methylcyclohexanone
6. Substitution reaction of the following S tosylate with cyanide ion yields a nitrile product (refer to the figure below).
What is the stereochemistry of the product? (10 seconds)

Answer: S stereochemistry

The reaction undergoes SN2 mechanism, hence, there is inversion of orientation. However, according to Cahn-Ingold-
Prelog rules, the product has an S stereochemistry.

7) 2,4,6-Trinitrotoluene or TNT is used as a high explosive and as a precursor in the manufacture of dyestuffs and
photographic chemicals. It can be prepared via nitration reaction of toluene. What do you call the intermediate formed in
this reaction? (10 seconds)

Answer: A carbocation

Its preparation is an example of a nitration reaction in which the aromatic ring undergoes electrophilic substitution. Only
the first step is shown below.

8. How many constitutional isomers are possible with molecular formula C 4H10O? (15 seconds)
*pano yung equation neto 

Answer: seven (7)

9. Poly(ethylene terephthalate) or PET is one of the known thermoplastics used for making plastic soft-drink bottles. Draw
the structures of its monomers. (30 seconds)

Answer:

10. The energy difference of 3.8 kJ/mol between gauche and anti butane corresponds to an equilibrium constant, Keq, of
approximately 1.9. Calculate the percentage of each conformer at equilibrium.

Answer: anti-65.5%, gauche-34.5%

Let X = fraction of anti butane conformation and

1 – X = fraction of gauche butane conformation

Since anti conformation is more stable than gauche conformation, the equilibrium constant expression is
X
K eq = =1.9
1−X
Then, solving for X gives 0.655 and 1 – X gives 0.345.

DIFFICULT

1. Given the following reaction. Draw the structure of the major product. (120 Seconds)
Pano yung mechanism neto 

Answer:

2. Given the following reaction. Draw the structure of the major product. (120 Seconds)

Answer:
3. Given the following reaction. Draw the structure of the major product. (150 Seconds)

Answer:

4. Given the following reaction. Draw the structure of the final major product. (150 Seconds)

Answer:
5. Give the IUPAC Name of the major product for the following reaction. (150 Seconds)

Answer: 3-Ethylpentane

6. What is the name of this reaction? (10 seconds)

Answer: Hofmann rearrangement

7. An unknown compound (X) contains only carbon and hydrogen, has MW= 112, and exhibits the spectral data below. In
addition to the IR signal listed below, there are only peaks corresponding to C–H stretches (between 3300 and 2900) and
several peaks in the “fingerprint region”. There are no overlapping peaks in either the 1H NMR or the 13C NMR spectra.
(120 seconds)

IR (cm-1) : 2145
13
C NMR (ppm) : 77.8, 70.1, 30.2
1
H NMR (ppm) : 2.45 (s)

When compound X was treated with excess n-BuLi (n-butyllithium) in tetrahydrofuran and then excess CH 3I
(iodomethane), a new compound (Y) with MW = 168 and 4 signals in its 13C NMR spectrum was formed. What are the
structures of X and Y?

Answer:

8. Give the product for the reaction below:

CH3C(CH3)2COOH
1. PBr3, Br2 ?
2. H2O
Answer: No reaction.
This is Hell-Volhard-Zelinskii reaction in which a carboxylic acid reacts with Br 2 and phosphorus to give an α-bromo
carboxylic acid. However, in the given molecule there are no α-hydrogens available for substitution.
*discuss mo to sir frank
9. Propose a structure for a compound with molecular formula C6H10O that fits the following spectroscopic data.
IR: 3400 cm-1(broad), 3250 cm-1(sharp), 2150 cm-1
1
H NMR: 1.0  (triplet, I=3), 1.5  (singlet, I=3), 1.6  (quartet, I=2), 2.5  (singlet, I=1), 3.4  (singlet, I=1)
13
C NMR: 5, 26, 35, 67, 69

Answer:

10. Suggest the structure of the product for the reaction below given the spectroscopic data:

MS: C12H16O2 ; IR: CH and fingerprint only

1
H NMR: (ppm) 7.25 (5H, s), 4.28 (1H, d, J = 4.8Hz), 3.91 (1H, d, J = 4.8Hz), 2.96 (3H, s), 1.26 (3H,s) and 0.76 (3H, s).

Answer: