SINHA IIT CHEMISTRY 1

TEST 2 GOC & POC

1 .For the compound shown below draw three other tautomers and explain why each is
less stable than the tautomer shown.
N

O N
H
2. Explain why imidazole is both a stronger acid and stronger base than pyrrole.
N

N N
H H

imidazole pyrrole
3.Consider Compound A below, and answer the questions that follow.
Br H
H3C C F
E IT A
C C
H I H

Y
H H
N

H3C CH3 TR
Compound A
SI

a. Put a star (*) by any chirality centers in Compound A.

b. Give the IUPAC name for Compound A.
IS
c. Draw an enantiomer of Compound A, if one exists. If Compound A does not have an
enantiomer, say so.
M

d. Does Compound A have any diastereomers? If so, how many does it have?
e. Does Compound A have an internal mirror plane? If so, indicate where it is.
f. A solution of 20.0g of Compound A in 100 mL of water produces a rotation of -40.0°
when placed in a 20 cm polarimeter cell. Calculate the specific rotation: show your work.

4. Answer the following questions as TRUE or FALSE. If the answer is false, explain
C

why it is false, and give an example.

a. If a structure is chiral, it must contain at least one chirality center.
b. If a structure contains only one chirality center, it is chiral.
c. If a structure has an enantiomer, it also has at least one diastereomer.
d. If a structure has a diastereomer, it also has an enantiomer.
5. How can you separate a pair of enantiomers?
A. Put them in a polarimeter, and use their optical rotations.
B. React them with another chiral molecule, and separate them by recrystallization or
chromatography.
C. Put them into a separatory funnel, and extract them with water that contains
deuterium, an isotope of hydrogen.
D Put them into a large magnetic field, and separate one to the positive pole, and the
other at the negative pole
6. Which of the halide ions is the best nucleophile in water?

1-D-10 Talwandi & B-7 JAWAHAR NAGAR,KOTA. 93149-05055

 SINHA IIT CHEMISTRY 2

a.Fluoride b. Chloride c.Bromide d.Iodide

7. Which carbocation below is the most stable?
A. B. C. D.
CH3 CH3 CH3 CH2 +

8. Which alkene below is the most stable?

A. B. C. D.

9. In an aqueous solution of pH = 7.0, the amino acid glutamine would be expected to be:
A) a fully ionized zwitterion with no net charge.
E IT A
B) a net positive ion due to protonation of the R group nitrogen.
H I H
C) a net negative ion due to deprotonation of the R group nitrogen.

Y
D) a totally neutral molecule with no net charge.
N

TR
10. For amino acids with neutral R groups, at any pH below the pI of the amino acid, the
population of amino acids in solution will:
SI

A) have positive and negative charges in equal concentration.

IS
B) show no net charge. C) have a net positive charge.
D) have a net negative charge.
11.Titration of leucine by a strong base results in two pKa values. The titration that occurs
M

at
pK2 is:
A) -COOH + OH- -COO- + H2O B) -COOH + -NH2 -COO- + -NH3+
C) -NH3+ + OH- -NH2 + H2O D) -NH2 + OH- -NH- + H2O
12.An octapeptide (GLY-ALA-GLY-ALA-GLY-ALA-GLY-ALA) has:
C

A) two free amino and two free carboxyl groups.

B) a single free amino group on an alanyl residue.
C) a single free amino group on an alanyl residue and a single free carboxyl group on a
glycyl group.
D) a single free amino group on a glycyl residue and a single free carboxyl group on an
alanyl
residue.
13.What will be the net charge of the tripeptide, LYS-HIS-TYR at pH 7.0?
A) +1 B) 0 C) -1 D) -2
14 Amino acids commonly found in turns and loops are:
A) ALA and GLY. B) PRO and GLY.
C) two CYS. D) those with ionizable R groups.

1-D-10 Talwandi & B-7 JAWAHAR NAGAR,KOTA. 93149-05055

 SINHA IIT CHEMISTRY 3

Problem 15: Nature’s building blocks

Natural rubber is a polymer composed of isoprene, the conjugated diene 2-methyl-1,3-butadiene. Isoprene
can be found not only in rubber but in a wide range of natural products called terpenes, most of which have
carbon skeletons made up of isoprene units joined head-to-tail. Recognition of this fact - the isoprene rule -
has been great help in working out structures and determining the biosynthetic origin of terpenes.
15-1. Find the isoprene units in the following terpenoid natural products.

OH OH

AcO O OH

O
O
R O OH OBz
E IT A OAc

In polymer chemistry, the repeating unit is called a monomer and the repeating units are joined together
H I H
through chain reaction polymerization or step-reaction polymerization. A few examples of step-reaction

Y
polymerization are provided below.
N

TR
15-2. Draw the repeating unit in each polymer product.
SI

COOH
HOOC heat
salt Nylon-6,6
IS
+
NH2
H2N
M

NCO
+ OH
HO Polyurethane

NCO
C

O
heat
O + HO OH Glyptal
OH
O

1-D-10 Talwandi & B-7 JAWAHAR NAGAR,KOTA. 93149-05055