EXAM # 1 Sample

Organic Chemistry I
2423

Amantadine-

an antiviral drug used as an antiviral

and
antiparkinsonic.

SAMPLE ORGANIC CHEM 2423 EXAM #1A

DIRECTIONS- Please answer all questions in the space provided as completely and clearly as possible .
Show all your work for the writing portions of the exam.
PART I- Multiple Choice (3 points each)
____1. How would you best describe the C-C bonds in H3C-CH2-CH3?
A. sp3-sp2
B. sp2-sp3
C. sp3-sp3
D. sp-sp
____2. Which of the following molecules contains an sp-hybrized C-atom?
A. CH2O
B. CH2CH2
C. CH3NH2
D. HCN
____3. Which of the following statement is(are) correct?
A. the maximum number of electrons possible for a set of p-orbitals is 6?
B. the ground state electron configuration of carbon 1s2 2s2 2px1 2py1 2pz0 .
C. the total number of bonding electron pairs in BF3 is 3.
D. All of these
____4. What is the formal charge on the N-atom in nitromethane, CH3NO2, in the
most important resonance forms of this molecule?
A. +1

B. 2

C. 1

D. +2

____5.Which one of the following IUPAC name does not represent an acceptable
name of propanol, C3H8O?
A. 1-Propaanol
C. 3-Propanol

B. 2-Propanol
D. All of them

____6. Which is the correct order of decreasing bond polarity? (Consider the
electronegativities of the halogens.)
A. H-F < H-Cl > H-Br > H-I
C. H-F > H-Cl < H-Br < H-I

B. H-F < H-Cl < H-Br < H-I

D. H-F > H-Cl > H-Br > H-I

____ 7. Which of the following conformation is the most stable conformation of butane, view the
molecule from the central carbons?

CH3

CH3

CH3

CH3

CH3

II

III

A. I only

B. II only

CH3

C. III only

D. all of these

____ 8. Which of the following cyclohexane conformation is(are) consider to be cis

conformation?

A. I only

III

II

B. II only

C. I and II

D. I, II, and III

____ 9. Which of the following isomers of pentane has a tertiary carbon?

A. 2-methylbutane
C. 2,2-dimethylpropane

B. n-pentane
D. None of these

____10. Which structure is tert.-butyl bromide?

A. Br-CH(CH3)-CH2-CH3
B. Br-C(CH3)3
C. Br-CH2-CH(CH3)2
D. Br-C(CH3)2-CH2-CH3
____11. Which one of the alkanes would you suspect to have the lowest boiling point?
A. 2-methylpropane

B. pentane

C. nonane

D. butane

____ 12. Which reaction describes the complete combustion of propane?

A.
B.
C.
D.

C3H8 + 5 O2
C3H8 + 3 O2
C3H8 + 3.5 O2
C3H8 + 4.5 O2

3 CO2 + 4 H2O
3 CO2 + 3 H2O
3 CO + 4 H2O
3 CO2 + 3 H2O

____13. Which conformation of cyclohexane corresponds to the most stable

structure?
A. half chair
B. chair
C. twist-chair
____14. Name the compound CH3-C(CH3)2-CClH-CH3 according to IUPAC
nomenclature.
A. 3-chloro-1,2-dimethylbutane
B. 3-chloro-2,2-dimethylbutane
C. 3-chloro-2,2-diethylbutane
D. 2-chloro-3,3-dimethylbutane
3

D. none of these

____15. Which of the following molecules can have Gauche interaction during rotation between C2 and C3.
A. Ethane
B. n-Butane
C. n-Propane
D. All of them
____16. An axial methyl group in cyclohexane suffers from what disadvantage?
A. one 1,3-diaxial interactions
C. two 1,3-diaxial interactions

B. two 1,2-diaxial interactions

D. one 1,2-diaxial interactions

____17. Among the following pairs of isomers, identify the pair of constitutional
isomers.
A. 2-Methlpentane and n-Hexane
B. 2-Methylbutane and n-Pentane
C. Ethanol and Diethylether
D. 1,2-Dimethylbutane and 2,2-dimethylbutane
E) All of them
____18. How many tertiary hydrogen atoms are there in Cl-CH2-C(CH3)2-CH(CH3)-C(CH3)3?
A. 6
B.3
C. 2
D. 1
____19. Consider the structure of trans-1,2-dimethylcyclohexane. Which statement
is fully correct?
A. Trans methyl groups favor chair and both are equatorial.
B. Trans methyl groups favor chair and both are axial.
C. Trans methyl groups favor the plane conformation.
D. Trans methyl groups favor chair and are axial and equatorial.
____20. Which statement is written incorrectly?
A. Acetic acid (pKa =4.73) is stronger acid than water(pKa =15.75).
B. The conjugate acid to (CH3)3N: is (CH3)3NH+.
C. An electron pair donor substance considers being a Lewis acid.
D. The stronger the acid, the lower the pKa value
PART II- Show your work (8 points each)
21. Name the Structures
CH3CH2

_______________________________

CH3

__________________________________

Structure of the names

cis- 1-ethyl-3-methylcyclohexane

5-ethyl-4-isopropyldecane

22. Draw all the possible resonances (at least two) for the following compound:
CH3
..

23. Identify the functional groups in the following compound and name each functional group.
CO - O - CH2 -CH3

O - CH = CH3

24. Complete the following reactions and write the possible products.
C6H14

+ O2

CH4

Cl2

25. Draw possible Newman projections and saw horse projections of nButane and indicate the most stable
conformer

BONUS Question(10 points)- Show all your work.

Please draw five isomers (constitutional or/and geometrical) of cyclobutane derivatives of the formula C5H9Cl.
Please name each isomer.

ORGANIC CHEM 2423 EXAM #1B ( Answers)

1. C 2. D 3. D 4. A 5. C 6. D 7. A 8. A 9. A 10. B
11. A 12. A 13. B 14. B 15. B 16. C 17. E 18. D 19. A 20. C
21. Naming: 3,4-diethyloctane
Structures :

trans 1-ethyl-3- methylcyclohexane

CH2CH3

CH3

22.
CH3

..

CH3

CH3

..

23.

CO - O - CH2 - CH3
ester

alkene
aromatic

O - CH = CH2
ether

24. 2C6H14 + 19O2

CH4
+ Cl2

12CO2 + 14H2O
CH3Cl + HCl

25. Refer to your notes

Bonus: Refer to your notes

..