SINHA’s I. I.T.

CHEMISTRY -1-

ORGANIC GOC DPP

1. What is the IUPAC name for the following molecule?

a) 2,4,5,7-tetramethylnonane
b) 1,1,3,5,6-pentamethylheptane
c) 3,5-dimethyl-isobutylhexane
d) 2,3,5,7-tetramethyloctane
e) 2,4,6,7-tetramethyloctane
2. Of the trimethylcyclohexanes shown below, which is lowest in energy?

3. Which of the following molecules has a dipole moment?

4. The carbon attached to the –OH functional group in cholesterol would be correctly classified as a ____________

carbon.
a) primary b) secondary c) tertiary d) quaternary e) penitentiary
5. Which of the underlined atoms in the molecules shown below have sp hybridization?
+
A. CH CHCH B. CH CCHCl C. CH CH D. HCCCH . E. CH CN F(CH ) CNNH
2 3 2 3 2 3 3 3 2 2
a) D and F b) D, E, and F c) A, C, and D d) B, D, and E e) A, B ,C, and F
2
6.In allene (H C=C=CH ), the terminal carbons are sp hybridized. Each of the terminal H C groups marks,
2 2 2
o
therefore, a plane, and the two "terminal" planes are 90 from each other. Other compounds with double bonds on
successive carbons may also exist. They are called cumulenes. What is the relationship between the two terminal
H C groups in a cumulene containing three consecutive double bonds (H C=C=C=CH )?
2 2 2
a) They are in perpendicular planes. b) They are in two planes 60° from each other.
c) They are in the same plane. d) They are in two planes 120° from each other. e)
o
They are in two planes 109 from each other.
7. A schematic representation of π-type molecular orbitals for 1,3,5-hexatriene (built out of six p atomic orbitals on
carbon atoms) is shown below. The orbitals are shown in a random order.

7a. Which orbital corresponds to the HOMO of 1,3,5-hexatriene?

7b. Which of the π orbitals have 2 nodal planes (in the bonding sense)

B-7. JAWAHAR NAGAR, KOTA.(RAJ) Ph-0744-2422383 .Mo-93149-05055

 SINHA’s I. I.T. CHEMISTRY -2-

8. Which of the following is not a resonance structure of the others?

9. How many constitutional isomers are there for the alkyl halide C H Cl?
5 11
a) 6 b) 7 c) 8 d) 9 e) 10
10. Which statement about the following equilibrium is true?

a) The equilibrium favors the products. b) t-Butoxide is the dominant anionic species in the equilibrium.
c) Water is the weaker acid. d) t-Butoxide is stabilized by resonance.
11. Which of the following is the product of the reaction between AlCl and CH OCH
3 3

12. Which molecule or ion has the longest C-N bond?

+ + +
a) H CNCH b) H CCN c) (H C) N d) (H N) C e) (H C) N
2 3 3 3 4 2 3 2 2
13. Which is an acceptable resonance structure for the following drawing?

14. Which statement is true regarding the following conformations for butane?

a) I is less stable than II because of steric strain b) III is less stable than I due to its torsional strain
c) III is called gauche conformation d) The steric strain in II is greater than in I
e) III has more energy than II

B-7. JAWAHAR NAGAR, KOTA.(RAJ) Ph-0744-2422383 .Mo-93149-05055

 SINHA’s I. I.T. CHEMISTRY -3-

ORGANIC GOC TEST-4

1.Which of the following isomeric structures has the lowest energy?

2.The compound with the formula of C4H10O contains the alcohol functional group (–OH), but has nomultiple bonds
or rings. How many constitutional isomers are possible for this alcohol?
a) 2 b) 3 c) 4 d) 5 e) 6 f) 7
3.Which of the following is not a valid resonance structure of the others?

4.. Which of the following molecules do not have a dipole moment?

a) A, D, E b) D, E c) A, B, C d) D, C e) B, D, E
5) Which of the underlined atoms (in the molecules shown below) are of sp2-hybridization type?
A: Cl CCCl B: CH3OCH3 C: CH3NH2 D: CH3COCH3 E: HCCH
2 2
a) A and D b) B and E c) A and C d) C and E e) B, C, and D
6. Consider the two chair conformations of cis-1-chloro-2-methylcyclohexane. Which of the following statements
about these two isomers is true?
a) Both conformations have equally unfavorable 1,3-diaxial interactions, resulting in no net energy difference .
b) The conformation with the methyl group in an equatorial position is more stable by 4.8 kJ/mol.
c) The conformation with the methyl group in an axial position is more stable by 5.2 kJ/mol.
d) The conformation with both substituents in equatorial positions is more stable by 10.4 kJ/mol.
e) The energy difference between both conformations cannot be established without knowing the value of Cl-CH3
gauche interaction.
7. Which of the following is the correct product of this reaction? (Lone electron pairs are not shown explicitly).

8. Which statement about the following equilibrium is true?

a) IV is a acting as a base b) II is acting as an acid

B-7. JAWAHAR NAGAR, KOTA.(RAJ) Ph-0744-2422383 .Mo-93149-05055

 SINHA’s I. I.T. CHEMISTRY -4-

c) I and III are resonance structures d) the equilibrium favors the reactants
e ) I is 14 times less acidic than IV
9. Which of the following molecules have dipole moments?
A: gauche conformation of 1,2-dibromoethane B: anti conformation of 1,2-dibromoethane
C: trans-1,4-dibromocyclohexane D: cis-1,4-dibromocyclohexane
E: tetrabromomethane F: dibromomethane
a) A and B b) A and D c) B and E d) C and F
e) A, D, and F f) A, C and E g) B, C and E h) B, D and E
10.Compare the hybridization of the central carbon atoms in carbon dioxide (CO2) and allene (H2CCCH2). Which
statement is correct?
a) The hybridization types of these two carbons cannot be compared because of large electronegativity difference
between carbon and oxygen in CO2 that does not exist in allene.
b) The hybridization of carbon in CO2 cannot be determined, because the lone electron pairs on oxygen do not allow
for angle measurements that are necessary to determine the hybrids involved.
c) In CO2 the carbon is sp2 hybridized, but in allene the central carbon is sp hybridized.
d) In CO2 the carbon is sp hybridized but in allene the central carbon is sp2 hybridized.
e) The central carbons in both compounds are sp hybridized.
11.Which of the following statements about molecular strain is correct?
a) Cis and trans stereoisomers of substituted cycloalkanes always have equal amount of strain.
b) Large angle strain is present in all cycloalkanes.
c) Gauche strain in butane is steric in origin.
d) All staggered conformations of small alkanes have torsional strain.
e) Strained alkanes yield less heat when burned in oxygen than their strain-free isomers.
12.Taking into account the standard conventions used to draw three-dimensional structures, which of the following
is the correct 3D representation of 2,3-pentadiene?

13. Which of the following statements about resonance structures is false?

a) Individual resonance structures are imaginary, not real.
b) Resonance forms differ only in the placement of their π or nonbonding electrons.
c) Different resonance structures of a substance don't have to be equivalent.
d) The superposition of resonance forms is always more stable than any individual resonance form.
e) In valid resonance structures, all atoms from the second row of the periodic table must have an octet of electrons.
14.Cycloalkanes with the formula of C6H12 have 12 different constitutional isomers. What is the maximum
number of tertiary carbons possible in any of them? a) 1 b) 2 c) 3 d) 4 e) 5
15. Dipole moments usually are measured on collections of molecules, and represent average values for all
conformations present. Which of the following collections of molecules will show a dipole moment (lone pairs are
not shown explicitly)?
A: ClH2CCH2Cl B: NH3 C: BF3 D: H3COCH3 E: (CCl3)2
a) A and C b) A and E c) B and C d) B and E e) A, B, and D f) A, C, and E g) B, C, and E
16 Taking into account hybridization
and resonance effects, rank the
following C-C bonds in order of
decreasing length.
a) A > C > D > B
b) D > B > C > A
c) C > A > D > B
d) A > C > B > D
e) B > D > C > A
17.Which one of the following isomeric structures has the lowest energy?

B-7. JAWAHAR NAGAR, KOTA.(RAJ) Ph-0744-2422383 .Mo-93149-05055

 SINHA’s I. I.T. CHEMISTRY -5-

18.Which statement about the following equilibrium is true?

a) The equilibrium favors III and IV.
b) I and III are resonance structures.
c) III is 3 times more acidic than II.
d) II is the conjugate acid of I.
e) IV is the strongest base in the system.
19. Which of the following molecules
would have the following potential energy
diagram for rotation about its central bond? Note: The 0o angle conformation was selected arbitrarily.
a) butane
b) 2-methylbutane
c) 2,3-dimethylbutane
d) 2,2,3-trimethylbutane

20. Which statement about strain is incorrect?

a) Strain energy is caused by imperfect bond lengths or angles.
b) Perfectly staggered bonds do not contribute to the torsional strain.
c) Cycloalkanes are puckered (except for cyclopropane) to minimize their torsional strain.
d) Strained compounds release less energy during combustion than their strain-free isomers.
e) Steric strain is defined as the repulsion that occurs when atoms are forced closer together than their van der Waals
contact distance.
21.Consider the following reaction of benzoic acid and titanium tetrachloride.

Which of the following is the main product of this reaction?

22. Which one of the following structures is not a resonance form of the others?

23.The H-N-H bond angle in ammonia (:NH3) is 107o. Compared to ammonia, what would be the expectation for
H-P-H bond angle in phosphine (:PH3)?
a) The bond angles will be essentially the same because phosphorus is in the same column of the periodic table as
nitrogen.
b) The bond angle would be larger because phosphorus needs more p-character in its hybrids to form its longer
bonds to hydrogen atoms.
c) The bond angle would be larger because phosphorous is bigger and needs more space for its bonds.
d) The bond angle would be smaller because phosphorous forms stronger bonds with hydrogen atoms.

B-7. JAWAHAR NAGAR, KOTA.(RAJ) Ph-0744-2422383 .Mo-93149-05055

 SINHA’s I. I.T. CHEMISTRY -6-

e) The bond angle would be smaller because phosphorus is less electronegative and needs more s-character in its
lone-pair hybrid.
24. Which of the following molecules have at least one sp hybridized carbon atom?

a) I, II, IV, VI b) II, III, IV, VI c) III, V, VI d) III, IV, VI

25. Which of the underlined atoms (in the molecules shown below) are of the sp3-hybridization type?
+
A: CH CH B: CH OCH C: CH CCH D: CH CCH E: CH CHCH
2 3 3 3 2 2 3 2
F: CO G: OCHCH H: CH CN I: CH NH
3 3 3 2
a) A and C b) F and H c) B and I g) C, D, F, and H
d) A, G, and I h) A, C, E, and G e) B, D, and H f) B, C, F, and G
26. Which of the following is not a valid resonance structure of the other three?

27. Which equilibrium is not rapid at room temperature?

28. Which of the following chair cyclohexane structures has the lowest energy?

29. What energy diagram would you expect for rotation about the central bond of 2-methylbutane?

B-7. JAWAHAR NAGAR, KOTA.(RAJ) Ph-0744-2422383 .Mo-93149-05055