UT Organic Chemistry Exam Practice

d. propanol
e. 2-propanol
I
4.4
i-i
I
1-4
1-4
I-I
d. 4-ethyl-3-methylhexene
e. 3-ethyl-4-propytheptane
d. pentane
e. hexane
‘
I
9. To which class does CHSCHINHl belong?
a. secondary amine
d. primary amide
b. primary amine
e. tertiary amine
c. secondary ainide
c.DNAandRNA
10. What do all organic chemists study?
a. ionic compounds
d. chemical rxn in plants
b. functional groups
e. chemical ran in mammals
19. Considering the same number of carbons, which
molecule would have the highest boiling point?
a. alkane
d. amine
b. aromatic
e. ether
c. alcohol
9Ø0
18. Which of the following statements is FALSE?
a. The most common bond angle in organic chemistry is
b. A condensed formula is the simplest way of representing the
structure of a linear hydrocarbon on paper.
c. The simplest cyclic hydrocarbon molecule contains three
carbon atoms.
d. A molecule of a cyclic hydrocarbon will have two less
hydrogen atoms than that of the linear hydrocarbon
having the same number of carbon atoms.
8. Which of the following compounds would be most miscible in
liquid decane?
a. methanol
d. propanone
b. propanol
e. propanoic acid
c. cyclopentane
7. When numbering the main chain or ring of an organic
compound, which functional group gets the highest priority?
a. methyl
d. ene
b. hydroxyl
e. yne
c. halogen
16. Which of the following statements is false?
a. Organic chemistry is the study of carbon compounds.
b. The properties of organic compounds are usually
determined by the functional group present.
c. Most small, organic compounds have low melting and
boiling points.
d. It is rare for a given molecular formula to represent more
than one or two organic compounds.
e. When an organic substance is burned in oxygen, carbon
dioxide and water are usually the major products.
15. What forms when water reacts with an alkene?
a. an ester
d. an amine
b. an acid
e. a ketone
c. an alcohol
.
14. Which statement describes an oxidation reaction in
organic chemistry?
a. The product has tcwer carbon-oxygen bonds than the
reactant.
b The product has one methyl group more than the reactant.
The product has more carbon-oxygen bonds than the
reactant.
ti. The product has more carbon-hydrogen bonds than the
reactant.
e. Ring structures usually form.
13. Which two compounds react to form an ester?
a. a carboxylic acid and an alcohol
b. an alcohol and an aldehyde
c. an alcohol and a ketone
d. a carboxylic acid and a ketone
e. an aldehyde and a carboxylic acid
12. What type of reaction is most common for benzene to
undergo?
a. substitution
d. reduction
b. hydrolysis
e. addition
c. oxidation
17. Which of the following statements is
a. Different compounds with the same molecular formula are
called isomers.
b. The most common intermolecular force for organic
molecules is hydrogen bonding.
c. The carbon atoms of organic compounds may join together
in long chains or rings.
d. In an electron-dot formula, four dots between a pair of
atoms represents a double bond.
e. Alkanes, alkenes, and alkynes are all aliphatic
hydrocarbons.
e. Use the electroneganvity values of each atom to determine the
polarity of each bond.
6. To predict whether or not an organic molecule contains a
polar bond, what do you not need to do?
a. Consider the three-dimensional shape of the molecule
b. Consider the bond dipoles within the molecule.
c. Determine if there is more than one single bond within the
molecule.
d. Determine if there is an imbalance in charge within the molecule.
a. propane
b. butane
c. methane
cl-I,
5. Which compound is a structural isomer of the compound
shown below?
4. Which feature do all aromatic hydrocarbons have?
a. an amine group
d. an aldehyde group
b. halogens
e. all double bonds in a ring
c. a benzene ring stnicture
a. 4-ethyl-3-methylheptane
b. 4-methyl-3-propylhexane
c. 3-propyl-4-methylhexane
I-.
I
1-4
1-4
1-4
T
T5T
I
I
I-4
1-4
-I
3. Name the following compound.
2. Which organic compound is saturated?
a. ethylcyclopentane
d. cyclohexane
e. l,3,5-lrimethyl-2-octene
b. 2-methyl-3-ethylpentyne
c. 1,1-dimethythexane
CH(OH)CH
CH
.
1. Name 3
a. iso-ethanol
b. tertiary-propanol
c. bulanol
I
11. What type of reaction occurs when bromine reacts
with pentyne to make dibromopentene?
a.substitution
d. reduction
b. isomerism
e. addition
c. oxidation
PART A: Multiple Choice: Answer on the scantron card provided (40)
Name:
Organic Chemistry Practice Test
d. methylbenzene
e. 6-methyl-I -hexene
a
sa ()
5
a
carcu,i_n
a
rs
—ca,
11
a
d. 3-methylhex-i-en-4-yne
c. 3-methylhex4-yn-1 -ene
b. 4-methylhex-2-yn-5-ene
a. 4-vinyl-2-pentyne
—CmC—CH—CH=CH
3
CH
2
40. What is the UJPAC name for the following compound?
CH3
28. What Is the major product expected from the following reaction?
rarrsc—H
39. Which compound will have H-bonding with itself?
a. 2-chlorobutane
d. 3-chiorobutanone
b. 2-chloro-2-butanol
e. benzene
c. N,N.diinethylethane
a
38. Which of the following can NOT undergo a
condensation reaction?
a. primary amine
d. secondary alcohol
b. primary alcohol
e. tertiary amine
c. tertiary alcohol
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.
e. It is a neutralization reaction.
36. Which compound is formed by the oxidation of a
tertiary alcohol?
a. tertiary alcohol
d. no reaction
b. aldehyde
e. ketone
c. carboxylic acid
35. What type of reaction is 3
CH,Cl +
3
CH + Cl
CH
-> CH
2
HO?
a. an addition reaction
d. an esterification reaction
b. a substitution reaction
e. an elimination reaction
c. a saponification reaction
34. The reaction CH
CHZ + H
2
-> 3
2
CH Is an example of
CH
a. substitution
d. fermentation
b. addition
e. oxidation
c. esterification
.
, the hydrogen atoms are spatially
4
33. In a molecule of CR
oriented toward the centers of a regular
pyramid
d. diamond
b. tetrahedron
e. hexagon
c. square
32. Which statement explains why the element carbon
forms so many compounds?
a. Carbon atoms combine readily with oxygen.
b. Carbon atoms have very high electronegativity.
c. Carbon readily forms ionic honda with other carbon atoms.
d. Carbon readily forms coalent bonds with other C atoms.
31. Compared to the rate of inorganic reactions, the rate of
organic reactions generally is
a. slower because organic particles are ions
b. slower because organic particles contain covalent bonds
c. faster because organic particles are ions
d. faster because organic particles contain covalent bonds
30. Which property is generally characteristic of an organic
compound?
a. low melting point
d. insoluble in nonpolar solvents
b. high melting point
e. conducts electricity
c. soluble in polar solvents
29. Which element is present In all organic compounds?
a. carbon
d. phosphorous
b. nitrogen
e. sulphur
c. oxygen
a. isoelectronic species
b. isotopes
c. steno isomers
d. These compounds are not related at all…they are totally different
27. How are the following compounds related?
a. 2-methylcyclohexene
b. 3-methylliexene
c. 1-methylcyclohex-2-ene
d. 3-methylcyclohexene
26. What is the best name for the following compound?
25. Which of the following compounds would have the highest
boiling point?
a. 3
F
2
CH
C
2
H d. CH
b. 2
e. 2
CH
CH
NH
3
CH
c. CH
OH
3
24. The coefficients of the balanced equation for the complete
combustion of propane are:
d.2,2,4,3
a.1,3,4,5
b.3,1,3,4
e.1,5,4.3
c. 1,5,3,4
23. The process for breaking large organic molecules into
smaller organic molecules is called
a. fractional distillation
b. reforming
d. cracking
c. polymerization
e. combustion
22. The name of the smallest possible ketone is
d. propanone
a. methanone
b. ethanone
e. butanone
c. methanal
21. Which of the following statements about the complete
combustion of ethyne is FALSE?
a. The reaction is highly exothermic.
b. The mole ratio of acetylene to carbon dioxide is 1 mole : 2
moles.
c. The other reactant is oxygen.
d. The reaction is slow because covalent bonds must be broken.
e. The reaction produces carbon dioxide and water.
20. Which of the following statements is false?
a. In general, as the number of carbon atoms increases, we observe
an increase in boiling points.
b. In the alkane class, branched chain isomers have higher boiling
points than their straight-chain isomers.
c. Molecules of straight-chain alkanes are tetrahedral at each
carbon.
d. As dispersion forces are the only type of intermolecular force
between alkane molecules, alkanes would not be miscible with
water.
e. Because of the weak intermolecular forces, alkanes have low
densities compared to water.
_________________
0
+
+
0
2
H
0
2
=CI-10H + H
2
0H
3
HCI —
Gl
2
CHcH
S0
2
H
4
/_al_cH_cH_cH_
NGH
2
H
C
3
CH
—
2
—OH
H + 3
———
Type of reaction
Class of organic product
r -, HBr +
9
H
4
C
2
B
CH
e.
d.
c.
2-methyl-2-propanol + (0) -.
2 —‘
b. benzene + Br
a.
–
—‘
3
0
2
N,N-dipropylethanainide + H
2-propanol + heptanoic acid
42. Using condensed structural diagrams, draw and name each missing item from the following reactions. (10)
ó)c ó ó
/c,l,_c*I\\
0
C11
—
2
3
C—NHCH
11 + 1120
I
0
3
CH
C
—
2
—0Na
H 4 1120
3
CH
C
—
2
—OH
H + NOH —
CHOHCH
CH
3
cH
3
CH
O
2
H
Reaction
41. Complete the following table. (10)
PART B: Reactions: Answer in the space provided.
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C
HO-—-()- —OH
200
20
40 60 80 100120140
Molecular mass (g/mol)
7.A
4
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)
o
b) Would your observations change if branched alkanes were included in this graph? Explain.
(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) What type of polymerization reaction is this? How do you know(2)
a) What is the structure of the repeating unit in polyester? (3)
HOC 2
—