Organic Chemistry Practice Test

Name:

PART A: Multiple Choice: Answer on the scantron card provided (40) I ‘

I
11. What type of reaction occurs when bromine reacts
1. Name 3 CH(OH)CH
CH
. with pentyne to make dibromopentene?
a. iso-ethanol d. propanol a.substitution d. reduction
b. tertiary-propanol e. 2-propanol b. isomerism e. addition
c. bulanol c. oxidation

2. Which organic compound is saturated? 12. What type of reaction is most common for benzene to
a. ethylcyclopentane d. cyclohexane undergo?
b. 2-methyl-3-ethylpentyne e. l,3,5-lrimethyl-2-octene a. substitution d. reduction
c. 1,1-dimethythexane b. hydrolysis e. addition
c. oxidation
3. Name the following compound.
-I 13. Which two compounds react to form an ester?
I-4 1-4 1-4 1-4 I-I
a. a carboxylic acid and an alcohol
I I I I b. an alcohol and an aldehyde
1-4
TI
1-4
T5T i-i 1-4 c. an alcohol and a ketone
4.4
d. a carboxylic acid and a ketone
e. an aldehyde and a carboxylic acid
I-.

a. 4-ethyl-3-methylheptane d. 4-ethyl-3-methylhexene 14. Which statement describes an oxidation reaction in

b. 4-methyl-3-propylhexane e. 3-ethyl-4-propytheptane organic chemistry?
c. 3-propyl-4-methylhexane a. The product has tcwer carbon-oxygen bonds than the
reactant.
4. Which feature do all aromatic hydrocarbons have? b The product has one methyl group more than the reactant.
a. an amine group d. an aldehyde group . The product has more carbon-oxygen bonds than the
b. halogens e. all double bonds in a ring reactant.
c. a benzene ring stnicture ti. The product has more carbon-hydrogen bonds than the
reactant.
5. Which compound is a structural isomer of the compound e. Ring structures usually form.
shown below?
cl-I, 15. What forms when water reacts with an alkene?
a. an ester d. an amine
b. an acid e. a ketone
c. an alcohol
a. propane d. pentane
b. butane e. hexane 16. Which of the following statements is false?
c. methane a. Organic chemistry is the study of carbon compounds.
b. The properties of organic compounds are usually
6. To predict whether or not an organic molecule contains a determined by the functional group present.
polar bond, what do you not need to do? c. Most small, organic compounds have low melting and
a. Consider the three-dimensional shape of the molecule boiling points.
b. Consider the bond dipoles within the molecule. d. It is rare for a given molecular formula to represent more
c. Determine if there is more than one single bond within the than one or two organic compounds.
molecule. e. When an organic substance is burned in oxygen, carbon
d. Determine if there is an imbalance in charge within the molecule. dioxide and water are usually the major products.

e. Use the electroneganvity values of each atom to determine the 17. Which of the following statements is
polarity of each bond. a. Different compounds with the same molecular formula are
called isomers.
7. When numbering the main chain or ring of an organic b. The most common intermolecular force for organic
compound, which functional group gets the highest priority? molecules is hydrogen bonding.
a. methyl d. ene c. The carbon atoms of organic compounds may join together
b. hydroxyl e. yne in long chains or rings.
c. halogen d. In an electron-dot formula, four dots between a pair of
atoms represents a double bond.
8. Which of the following compounds would be most miscible in e. Alkanes, alkenes, and alkynes are all aliphatic
liquid decane? hydrocarbons.
a. methanol d. propanone
b. propanol e. propanoic acid 18. Which of the following statements is FALSE?
c. cyclopentane a. The most common bond angle in organic chemistry is 9Ø0

b. A condensed formula is the simplest way of representing the

9. To which class does CHSCHINHl belong? structure of a linear hydrocarbon on paper.
a. secondary amine d. primary amide c. The simplest cyclic hydrocarbon molecule contains three
b. primary amine e. tertiary amine carbon atoms.
c. secondary ainide d. A molecule of a cyclic hydrocarbon will have two less
hydrogen atoms than that of the linear hydrocarbon
10. What do all organic chemists study? having the same number of carbon atoms.
a. ionic compounds d. chemical rxn in plants
b. functional groups e. chemical ran in mammals 19. Considering the same number of carbons, which
c.DNAandRNA
molecule would have the highest boiling point?
a. alkane d. amine
b. aromatic e. ether
c. alcohol
 _________________

20. Which of the following statements is false? 29. Which element is present In all organic compounds?
a. In general, as the number of carbon atoms increases, we observe a. carbon d. phosphorous
an increase in boiling points. b. nitrogen e. sulphur
b. In the alkane class, branched chain isomers have higher boiling c. oxygen
points than their straight-chain isomers.
c. Molecules of straight-chain alkanes are tetrahedral at each 30. Which property is generally characteristic of an organic
carbon. compound?
d. As dispersion forces are the only type of intermolecular force a. low melting point d. insoluble in nonpolar solvents
between alkane molecules, alkanes would not be miscible with b. high melting point e. conducts electricity
water. c. soluble in polar solvents
e. Because of the weak intermolecular forces, alkanes have low
densities compared to water. 31. Compared to the rate of inorganic reactions, the rate of
organic reactions generally is
21. Which of the following statements about the complete a. slower because organic particles are ions
combustion of ethyne is FALSE? b. slower because organic particles contain covalent bonds
a. The reaction is highly exothermic. c. faster because organic particles are ions
b. The mole ratio of acetylene to carbon dioxide is 1 mole : 2 d. faster because organic particles contain covalent bonds
moles.
c. The other reactant is oxygen. 32. Which statement explains why the element carbon
d. The reaction is slow because covalent bonds must be broken. forms so many compounds?
e. The reaction produces carbon dioxide and water. a. Carbon atoms combine readily with oxygen.
b. Carbon atoms have very high electronegativity.
22. The name of the smallest possible ketone is c. Carbon readily forms ionic honda with other carbon atoms.
a. methanone d. propanone d. Carbon readily forms coalent bonds with other C atoms.
b. ethanone e. butanone
c. methanal 33. In a molecule of CR
, the hydrogen atoms are spatially
4
oriented toward the centers of a regular
23. The process for breaking large organic molecules into . pyramid d. diamond
smaller organic molecules is called b. tetrahedron e. hexagon
a. fractional distillation c. square
b. reforming d. cracking
c. polymerization e. combustion 34. The reaction CH
CHZ + H
2 -> 3
2 CH Is an example of
CH
a. substitution d. fermentation
b. addition e. oxidation
24. The coefficients of the balanced equation for the complete c. esterification
combustion of propane are:
a.1,3,4,5 d.2,2,4,3 35. What type of reaction is 3
CH + Cl
CH -> CH
2 CH,Cl +
3
b.3,1,3,4 e.1,5,4.3 HO?
c. 1,5,3,4 a. an addition reaction d. an esterification reaction
b. a substitution reaction e. an elimination reaction
c. a saponification reaction
25. Which of the following compounds would have the highest
boiling point?
36. Which compound is formed by the oxidation of a
a. 3CH
C
2 H d. CH F
2 tertiary alcohol?
b. 2NH
3
CH e. 2
CH
CH a. tertiary alcohol d. no reaction
c. CH
OH
3 b. aldehyde e. ketone
c. carboxylic acid

26. What is the best name for the following compound? 37. Which statement describes an esterification reaction?
a. It involves a carboxylic acid and an alkane.
b. it is a type of hydrolysis reaction.
c. It is a reduction reaction.
d. It is a type of condensation reaction.
a. 2-methylcyclohexene d. methylbenzene e. It is a neutralization reaction.
b. 3-methylliexene e. 6-methyl-I -hexene
c. 1-methylcyclohex-2-ene 38. Which of the following can NOT undergo a
d. 3-methylcyclohexene condensation reaction?
a. primary amine d. secondary alcohol
27. How are the following compounds related? b. primary alcohol e. tertiary amine
c. tertiary alcohol

a. isoelectronic species 39. Which compound will have H-bonding with itself?
a. 2-chlorobutane d. 3-chiorobutanone
b. isotopes
b. 2-chloro-2-butanol e. benzene
c. steno isomers c. N,N.diinethylethane
d. These compounds are not related at all...they are totally different a
40. What is the UJPAC name for the following compound?
28. What Is the major product expected from the following reaction? CH3
sa () —CmC—CH—CH=CH
3
CH
2
rarrsc—H

a. 4-vinyl-2-pentyne
b. 4-methylhex-2-yn-5-ene
a carcu,i_n rs
—ca,
11
5 a a a c. 3-methylhex4-yn-1 -ene
d. 3-methylhex-i-en-4-yne
PART B: Reactions: Answer in the space provided.

41. Complete the following table. (10)

Reaction Type of reaction Class of organic product

cH
3
CH
O
2 H + HCI —
Gl
2
CHcH + 0
2
H

CHOHCH
CH
3
=CI-10H
2
0H
3 + 0
2
H

0
3
CH
C
—
2 —OH
H + NOH —

3
CH
C
—
2 —0Na
H 4 1120

0
I S0
2
H
4
0
C11
—
2
3 C—NHCH
11 + 1120 ———

C
3
CH
—
2 —OH
H + NGH
2
H
3

/c,l,_c*I\\ /_al_cH_cH_cH_

ó)c ó ó
42. Using condensed structural diagrams, draw and name each missing item from the following reactions. (10)

a. 9
H
4
C
-
2
B r
CH -, HBr +

b. benzene + Br
2 —‘

c. —‘ 2-propanol + heptanoic acid

d. - N,N-dipropylethanainide + H
0
2

e. 2-methyl-2-propanol + (0) -.

3
 PART C: Short Answer: Choose a combination of questions so that the total number of marks equal 15
marks. The mark value of the question is provided after each question. You cannot break up questions.
CLEARLY NUMBER AND ANSWER ON NEXT PAGE. The first 15 marks will count!

43. Describe dispersion forces, and explain how they affect the physical properties of organic molecules. (2)

44. Suggest a reason why benzene may not be as reactive as other hydrocarbons, which also have double bonds.
Hint: Consider the electron arrangement in the double bonds of benzene. (3)

45. Identify each type of reaction in the following diagram. (6)

46. Polyester is made from the following monomers.

HOC 2
—<J)--CH
H
o H HO-—-()- —OH

a) What is the structure of the repeating unit in polyester? (3)

b) What type of polymerization reaction is this? How do you know(2)

47. a) State the trends in the bulling points of straight-chain alkanes, as shown in the following graph, and explain these trends.
(3)

b) Would your observations change if branched alkanes were included in this graph? Explain.
(2)

o 200

7.A
20 40 60 80 100120140
Molecular mass (g/mol)

48. Draw two different diagrams of the benzene molecule. Explain what each diagram shows, and state which diagram is
thought to be more correct. (4)