1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
KING FAHD UNIVERSITY OF PETROLEUM & MINERALS
Organic Chemistry I (CHEM 201)
Major Exam # 1, Term 111 Wednesday, Oct. 19, 2011
TIME: 2 hours
Dr. Bassam El-Ali (Sec. 1)
Dr. Musa Musa (Sec. 2)
Dr. Muhamamd R Imam (Sec. 3)
Dr. Nisar Ullah (Sec. 4)
Dr. Rami Suleiman (Sec. 5)
Name……………………….….
ID#……………
1
3
2
H
Li 4Be 5B
11
Sec. #……
6
C
7
N
8
O
9
Value
18
18
26
38
100
F 10Ne
Na 12Mg 13Al 14Si 15P 16S 17Cl 18Ar
35
Question
1-3
4-6
7-9
10 - 14
Total
Br
53
Score
0
He
I
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
(4 + 4 + 4 pts)
Q1.
A) Draw a correct Lewis structure for molecular formula (CH3)3NO and calculate the
formal charges on N and O atoms.
B) Arrange the following covalent bonds in the order of decreasing polarity.
(Most polar first)
(a)
CN
(b)
HO
(c)
CO

Most polar
(d)
HC
Least polar
C) Arrange the following compounds in the order of decreasing boiling points.
(Highest first)
OH
O
N
H
(c)
(d)
OH
(a)
Highest
(b)

1
Lowest
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
(4 pts)
Q2. Complete the following acid-base reactions. Draw correct structures in the
appropriate boxes.
O
(a) H3C C OH
(b)
NH2
conjugated acid
conjugated base
conjugated acid
conjugated base
CH3CH2OH
N
(2 pts)
Q3. Identify the Lewis acid and Lewis base in the following chemical reaction:
CH3
H3C C
CH3
CH3 H
H3C C O
CH3 H
H2O
(3 + 1 pts)
Q4.
A) Draw two resonance structures of the following anion by drawing appropriate arrows,
showing movement of electrons.
O
O
2
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
B) Identify the major and minor contributors of the following resonance structures.
H 2C
C
N
H 2C
C
N
(8 pts)
Q5. For the following given structure, determine
B
H3CO
N
H
O
HO
A
(I) How many π bonds does this molecule have?
(II) What is the hybridization of nitrogen atom and carbonyl oxygen in the molecule?
N
O
(III) Which bond is longer, A or B
(IV) Identify all the functional groups enclosed in the boxes.
1.
_______________________
2.
_______________________
3.
_______________________
4.
_______________________
3
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
(6 pts)
Q6.
A) What hybrid orbitals or atomic orbitals are used to form the indicated sigma
bonds?
6
4
2
CH 3
H
:N
C
N
C CH
N
O
C
C
C
NH2
OH
8
1
5
3
7
1.
___________________
2.
___________________
3.
___________________
4.
___________________
5.
___________________
6.
___________________
7.
___________________
8.
___________________
4
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
(4 + 6 pts)
Q7.
A) Write the correct class name for each of the following structures from this list.
ketone, alcohol, carboxylic acid, amide, alkyne, ester, ether, aldehyde, amine, or
alkene.
H
a)
O
b)
N CH3
O
O
c)
O
d)
N H
B) Each of the following names given below is incorrect. Write the structure that
corresponds to each of these incorrect names and then give its correct IUPAC name.
a) 2-Isobutyl-3-methylhexane
b) 2,2-Diethylbutane
c) 2-tert-Butylpentane
5
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
(4 + 4 pts)
Q8.
A) Write the structure for each of the following IUPAC names.
I)
2-Bromo-1-sec-butyl-4-isopropylcyclohexane
II)
6-Hydroxy-5-isobutyl-8-iodooctanal
B) Write four structural cyclic isomers for the molecular formula C3H5N
6
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
(8 pts)
Q9. Write the IUPAC name for each of the following compounds:
Br
O
a)
OH
OH
Cl
b)
OH
O
c)
NH2
OH
d)
NO2
F
7
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
(3 + 6 + 6 pts)
Q10.
A) Tetracycline is a broad-spectrum antibiotic because it is active against a wide variety
of bacteria. How many chiral carbons does tetracycline have?
H3 C
H 3C
OH
H
N
H
CH3
OH
NH 2
OH
O
OH
OH
O
O
write your Answer here
B) Identify the following alkenes as (E) or (Z).
O
O
H
O
O
O
H
H
F CH2
Br
O
O
N
H
Cl
C) Assign each of the following molecules as an (R) or (S) configuration.
CO2H
OH
CH2 F
O
Cl
H
O
H
8
H
O
CH2NH2
O
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
(4 pts)
Q11. Draw Newman projections for
A) The most stable staggered conformation around the indicated C-C bond.
H 3C
CH 3
H
H 3C
H
CH 3
most stable staggered
B) The least stable eclipsed conformations around the indicated C-C bond.
Br
Br
Cl
least stable eclipsed
(5 + 4 pts)
Q12.
A) Draw chair conformers for the more stable and less stable trans-1-tert-butyl-3methylcyclohexane.
less stable CHAIR conf ormer
t rans-1-ter t-butyl-3-methylcyclohexane
more stable CHAIR conf ormer
t rans-1-ter t-butyl-3-methylcyclohexane
9
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
B) Differentiate the following compounds as chiral, achiral or meso.
OH
Br
CH3
Br
CH3
Br
HO
OH
(4 pts)
Q13. For the following structural formula, draw a pair of enantiomers and a pair of
diastereomers.
OH
H
OH
O
OH
A) A pair of enantiomers
B) A pair of diastereomers
10
1st Major Exam: Organic Chemistry I (CHEM 201) Term-111
Oct. 19, 2011
(6 pts)
Q14. For the structures given below, fill up the blanks by using the appropriate listed
words:
H
H3C
C
Cl
C
OH
CH3
H
A
C
Cl
CH3
C
C
H3C
OH
H3C
OH
H
H
H
Cl C
B
H
C
Listed words:
diastereomers
identical compounds
enantiomers
(i) A and B are _________________________________
(ii) A and C are _________________________________
(iii) B and D are _________________________________
(iv) B and C are _________________________________
11
CH 3
H
HO
H3C
C
C
H
D
CH3
Cl