ORGANIC CHEMISTRY POST TEST

Answer the following questions:

Test I.

1. How many electrons occupy the bonding molecular orbitals

of a CN triple bond?
A) 2 B) 4 C) 6 D) 8

2. Which of the following species is not amphoteric ?

A) NH3 B) HF C) NH4(+) D) HCO3(-
)

3 What is the relationship of the two structures shown

below?

A) they are identical.

B) they are conformations of the same structure
C) they are constitutional isomers.
D) they are different compounds with different
compositions

4 Which of the following molecules will not have a dipole

moment?
A) CH3Cl
B) CH3OCH3
C) CH2Cl2
D) CCl4

5 Which of the following molecules has a dipole moment?

A) CBr4
B) CH2=CH2
 C) BF3
D) SO2

6 Which of the following molecules has a linear shape?

A) NH3
B) H2S
C) CO2
D) H2CO

7 Which of the following intermediates is pyramidal in

shape?
A) H3C(+)
B) H2C:
C) H3C:(-)
D) HC≡C:(-)

8 In which compound does carbon have the highest oxidation

state?
A) CH4
B) HCN
C) H2CO
D) CH2Cl2

9 Which of the following statements applies to a

C10H14O2 compound?
A) it may have 2 double bonds and 2 rings
B) it may have 3 double bonds and 0 rings
C) it may have 1 triple bond and 3 rings
D) it may have 0 double bonds and 3 rings
10 What functional group is present in the terpene camphor?

A) hydroxy
B) carboxy
C) carbonyl
D) oxy

11 What functional class is represented by the alkaloid

coniine?

A) amine
B) imine
C) amide
D) nitrile

12 Which of the following compounds would be considered an

electrophilic reagent?
A) NH3
B) Br2
C) CH3OH
D) NH2OH

13 Which of the following compounds would you expect to be

most soluble in water?
A) CH2Cl2
B) C6H12 (cyclohexane)
C) CH3CH2OH
D) C2H5OC2H5
14 The following compounds have similar molecular weights.
Which has the highest boiling point?
A) CH3CH=O
B) C2H5OH
C) CH3OCH3
D) CH3CH2CH3

15 Which of the following compound pairs are constitutional

isomers?
A) CH3CH2OCH3 and CH3CH2CHO
B) CH3CH2CHO and CH3CH2CH2OH
C) CH3COCH2CH3 and CH3CH2COCH3
D) CH3CH2CH2CHO and CH3COCH2CH3

16 Which of the following compounds may be classed as a

protic solvent?
A) tert-butanol
B) diethyl ether
C) n-hexane
D) acetone

17 Classify the following reaction.

A) substitution
B) addition
C) elimination
D) rearrangement

18 Which of the following is not a nucleophile?

A) H2O
B) CH3NH2
 C) C2H5SH
D) C6H12 (cyclohexane)

19 Which of the following is not an electrophile?

A) C2H5OC2H5
B) BF3
C) [CH3]3C(+)
D) HOCl

20 Which Lewis formula is the best representation of N2O?

(A) (B) (C) (D)

21 Which of the following compounds has a C-H bond with the

lowest bond dissociation energy?
A) C2H6
B) C6H6
C) C2H2
D) CH3CH=CH2

22 In order for a reagent to behave as a nucleophile

it must have ...
A) an overall positive charge.
B) an overall negative charge.
C) a non-bonding electron pair.
D) a nitrogen or sulfur atom.

23 The H–C–O bond angle in H2C=O (formaldehyde) is

approximately .....
 A) 90º
B) 109º.
C) 120º.
D) 180º.

24 Which of the following structural pairs represents

contributors to a resonance hybrid?

25 Which of the following molecular formulas is reasonable

for a stable compound?
A) C8H14O2Cl
B) C6H14Br2
C) C7H10NF
D) C30H54N2Cl

26 What formal charges are present in the molecule C6H5C≡N-

O?
( all heavy atoms have a valence shell octet, and C6H5- is
a phenyl group)
A) N is -1 and C is +1
B) N is +1 and C is -1
C) O is -1 and C is +1
D) O is -1 and N is +1
27 Which statement about members of a homologous series is
true ?
A) they are all constitutional isomers.
B) they are always hydrocarbons.
C) each differs from its nearest neighbors by 14 amu.
D) they may also be classified as tautomers.

28 How many structurally distinct (different) sets of

hydrogens are present in (CH3)3CCH2OCH3?
A) 2
B) 3
C) 4
D) 8

29 The pKas of H2CO3 are 6.4 & 10.3. The pKa of HOBr is 8.7.
If equimolar amounts of Na2CO3 and HOBr are dissolved in
water what will be the predominant anionic species in the
resulting solution?
A) HCO3-1 and BrO-1
B) CO3-2, Br-1 and OH-1
C) HCO3-1 and Br-1
D) CO3-2 and 2 BrO-1

30 Which of the following is a conjugate base of CH3NHOH?

A) CH3NH-1
B) CH3NHO-1
C) CH3NH3+1
D) CH2=NOH-1
31 A Lewis formula for diazomethane, CH2N2, is shown on the
left below.
Which of the formulas within the brackets would be
considered a proper resonance contributor to this structure
?

32 The curved arrows in the formula on the left represent a

chemical reaction.
Which of the formulas within the brackets would constitute
the product(s) from this reaction ?

33 Which of the descriptions (A to D) correctly describe

the following energy diagram?

A) A two-step exothermic reaction having an

activation energy = X
B) A two-step endothermic reaction having an
activation energy = Y
C) A two-step exothermic reaction having an
activation energy = Y
D) A two-step endothermic reaction having an
activation energy = X

34 Which of the following series contain a free radical, a

nucleophile and an electrophile?
A) Br· BF3 NH3
B) NH3 NO2+ Br2
C) H2O Cl· NH3
D) Cl2 CH4 NH3
35 The curved arrows in the formula on the left represent a
chemical reaction.
Which of the formulas within the brackets would constitute
the product(s) from this reaction ?

36 Which of the following species has a planar molecular

configuration?
A) SO3-2
B) SO3
C) SOCl2
D) SO2Cl2

37 Which of the following compounds does not have a planar

molecular configuration?
A) H2C=CH2
B) H2C=CH–C≡CH
C) H2C=C=CH2
D) H2C=C=C=CH2

38 How many degrees of unsaturation does the following

structure have?

A) 4
B) 5
C) 6
D) 7
39 The structural formula for vitamin C is shown below
Of the four hydroxyl groups, identified by shaded
circles, which is most acidic?

A) 1
B) 2
C) 3
D) 4

40 Which of the following structures is not a resonance

contributor to the hybrid defined by the other three?

41 The following structures are resonance contributors for

a reactive intermediate formed during ozonolysis of
alkenes.
Identify the most energetically favorable and the least
favorable contributors?

A) III is most favorable & II is least favorable

B) I is most favorable & IV is least favorable
C) II is most favorable & IV is least favorable
D) I is most favorable & II is least favorable
42 How would the bond strength of the C:C double bond in an
alkene compare to that of a C:C single bond in the
corresponding alkane?
A) The double bond would have the same strength as the
single bond.
B) The double bond would be stronger than, but less than
twice as strong as the single bond.
C) The double bond would have exactly twice the strength
of the single bond.
D) The double bond would have more than twice the
strength of the single bond.

43 Which of the following cations is most stable?

A) FH2+
B) OH3+
C) NH4+
D) CH5+

44 The toxic environmental pollutant dioxin is 44.8%

carbon, 1.25% hydrogen and 44.0% chlorine. Its molecular
weight is 320±10
What is the molecular formula of dioxin?
A) C10H8O4Cl4
B) C12H6O2Cl4
C) C6H2OCl2
D) C12H4O2Cl4

45 Which of the following covalent compounds does not have

any formally charged atoms?
A) (CH3)3NO
B) CH2=N=N
C) CH3-O-N=O
D) CH3C≡NO
46 Which of the following statements is not generally
correct?
A) endothermic reactions have larger energies of
activation than exothermic reactions
B) the rate of a reaction is proportional to its
activation energy
C) the rate of a reaction generally increases as the
temperature is raised
D) all reactions in which bonds are broken and formed
have a significant activation energy

47 Which of the following compounds has no isomer?

A) CH3CH2CH2Cl
B) CH3CHO
C) CH2=CHCl
D) ClCH2CH2Cl

48 Which of the following statements about carbon is

not correct?
A) carbon forms strong covalent bonds to itself,
allowing chains and rings to be made.
B) carbon expands its valence shell to accomodate more
than eight electrons and thus forms double and triple
bonds.
C) carbon forms strong covalent bonds to elements like
nitrogen and oxygen because it does not have lone pairs of
valence electrons to destabilize the bonds.
D) carbon and hydrogen have similar electronegativity
and form strong bonds to each other, thus avoiding the high
reactivity shown by metal hydrides.

Test II

1. Organic Chemistry is the study of ________________.

2. What is the difference between an alkane, alkene and
alkyne?

3. Label the following as cis- or trans- isomers with

respect to chlorine:

4. Draw the general structure of an ester:

5. List several objects that you use each day that is made
up of polymers.

6. Define the term “polymer”.

7. Give one example of a naturally found polymer.