Organic Chemistry

1. Which is not a structural isomer of

CH3CH2COOH?
A. CH3CH2COOCH3
B. CH3COOCH3
C. CH3COCH2OH
D. HOCH=CHOCH3
E. CH3CH(OH)CHO

2. Which is a structural isomer of CH3CH2COOH

that has a lower boiling point?
A. CH3CH2COOCH3
B. CH3COOCH3
C. CH3COCH2OH
D. HOCH=CHOCH3
CH
C
B
3
2
3C
3
3
C.
D
OH
C
C
2
2
A. OH

7. Which of the following compounds is a structural

isomer of one or more of the other compounds and
also exhibits geometrical isomerism?
A. H2C=CHCH2CH2CH3
E. CH3CH(OH)CHO B. CH3CH=CHCH2CH3
C. H2C=CHCH=CHCH3
D. (CH3)2C=CHCH3
3. Which is a structural isomer of CH3CH2COOH
that exhibits optical isomerism?
A. CH3CH2COOCH3
B. CH3COOCH3 8. Which of the following has the lowest vapor
C. CH3COCH2OH pressure at 25 °C.
D. HOCH=CHOCH3 O
E. CH3CH(OH)CHO a. CH3CH2–O–CH 2CH3 b. CH3CH2CH2CH

4. Which is a structural isomer of CH3CH2COOH c. CH3CH2CH2CH2OH d. CH3CCH2CH3

that exhibits geometric isomerism?
A. CH3CH2COOCH3
B. CH3COOCH3
C. CH3COCH2OH 9. Which liquid would you expect to have the
D. HOCH=CHOCH3 highest viscosity at room temperature?
E. CH3CH(OH)CHO A. n-octane
B. isooctane
C. 2-octanone
5. Which is a structural isomer of CH3CH2COOH D. octanoic acid
that does not exhibit optical isomerism and has the
following IR spectrum: 10. Predict the length of each NO bond in
nitrobenzene (C6H5NO2)). [The NO single bond
length is 146 pm, the N=O double bond length is
121 pm.]
A. 110 pm
B. 121 pm
C. 130 pm
D. 146 pm

A. CH3CH2COOCH3
B. CH3COOCH3 11. According to the IUPAC rules, the following
C. CH3COCH2OH compound can be named:
D. HOCH=CHOCH3
E. CH3CH(OH)CHO

6. Which of the following has four stereoisomers?

A. 1,3-cycloheptadiene
B. 3,5-cyclohexadiene
 C. 1,3-dicyclohexene B. 1
D. 1,3-cyclohexadiene C. 2
E. 3,5-cyclopentadiene D. 3
E. 4

12. Name the following compound:

17. Which of the following are geometric isomers?

A. 4-ethyl-5-methylhexane
(I) (II)
B. 2-methyl-3-propylpentane
C. 2-methyl-3-ethylhexane
D. 4-methyl-3-propylpentane
E. 3-ethyl-2-methylhexane
(III)
A. I and II
B. II and III
13. How many isomers are there corresponding to C. I and III
the formula C4H10O? D. none of these compounds exhibit
geometric isomerism
A. 3
B. 5
C. 6
D. 7
E. 9 18. Which type of organic compound contains a
hydroxyl group?
14. Which of the following formulas represent A. ethers
different molecules? B. carboxylic acids
A. C. esters
D. ketones
E. aldehydes

B.

19. Select the correct name for the following

C. compound.
CH2 CH3

D.

Cl
A. 1-chloro-5-ethylcyclohexene
15. The correct name for the following compound B. meta-chloroethylcyclohexene
is: C. 1-chloro-5-ethylbenzene
CH2 —CH3 D. meta-chloroethylbenzene

CH—CH—CH2 —OH
20. Identify the products for the reaction between
cyclohexene and bromine.
CH3 CH3
A. 2,3,4-trimethyl-1-butanol
B. 3,4-dimethyl-5-pentanol + Br2
C. 3-ethyl-2,3-dimethyl-1-propanol
D. 2,3-dimethyl-1-pentanol
Br

+ H2
16. Tartaric acid, HO2CCHOHCHOHCO2H, is a
dihydroxycarboxylic acid. How many chiral centers
does its structure(s) posses? A. Br
A. 0
 CH3 O

+ 2HBr

B. HO C—H
Br
O
A. amine
B. ketone
Br C. carboxylic acid
C. D. alcohol
H E. aldehyde

+ HBr

D. Br
26. Distillation separates components of a mixture
due to differences in
  a. vicosity
21. The reaction of HCl(g) with CH3 - CH = CH2   b. boiling points
will yield as the main product   c. melting points
A. ClCH2CH=CH2   d. solubility
B. CH3CH2CH2Cl   e. octane ratings
C. CH3CH=CHCl 27. Long-chain hydrocarbons are converted into
D. CH3CCl=CH2 smaller-chain molecules by a process called
E. CH3CHClCH3   a. fractionation.
  b. catalytic reforming.
  c. catalytic cracking.
  d. converting.
22. Cycloalkanes have the general formula   e. distillation.
A. CnH2n 28. The process of fractional distillation is used to
B. CnH2n+2   a. completely separate the many
C. C2nH2n components of a complex mixture.
D. CnHn+2   b. partially separate the many components
E. CnH2n-2 of a complex mixture.
  c. break large molecules in a mixture into
smaller ones, and completely separate
them.
23. Which one of the following is the formula for a   d. separate the two components of a
ketone? simple mixture.
A. CH3CH2CHO   e. break large molecules in a mixture into
B. CH3OCH3 smaller ones, and partially separate
C. CH3CH2COCH3 them.
D. CH3CH2COOH 29. The principal component of natural gas is
E. H2C=C=CH2   a. ethane.
  b. butane.
  c. propane.
  d. methane.
24. Under mild conditions, oxidation of the primary   e. none of these choices.
alcohol CH3CH2CH(OH) will produce a/an 30. The laboratory separation of a mixture of
A. aldehyde substances by gas chromatography is related to
B. amine   a. catalytic reformation.
C. alkene
  b. pyrolytic decomposition.
D. ketone
E. carboxylic acid   c. simple distillation.
  d. catalytic cracking.
  e. fractional distillation.
31. In gas chromatography, volatile compounds in a
25. Vanillin is used as a flavoring agent. Identify mixture are separated by their
the functional group circled.   a. interactions with a stationary liquid
 phase in a column.   b. ketones; aldehydes; no reaction
  b. mass.   c. ketones; no reaction; aldehydes
  c. density.   d. aldehydes; no reaction; ketones
  d. diffusion rates through a semipermeable   e. aldehydes; ketones; no reaction
polymer membrane. 37. A primary alcohol oxidizes in two stages to
  e. boiling points. produce a(an) _____. This same product can also
32. How many carbons in the structure shown be obtained by oxidation of a(an) _____.
below are not chiral?   a. aldehyde; ketone
  b. carboxylic acid ; aldehyde
  c. tertiary alcohol ; secondary alcohol
  d. aldehyde; secondary alcohol
  e. carboxylic acid ; ketone
38. The functional group in which a carbon atom
has a single bond to a hydroxyl group, a single
  a. 5 bond to each of two other carbons, and a single
  b. 2 bond to a hydrogen is the _____ functional group.
  c. 3   a. tertiary alcohol
  d. 4   b. secondary alcohol
  e. 6   c. ketone
33. Consider the carbon skeleton shown below. If a   d. primary alcohol
_____ group is attached to carbon 4, a _____   e. aldehyde
alcohol will result; if the group is attached to carbon 39. The sequence of compound classes in the
6, a _____ alcohol will result. oxidation of ethanol would be
  a. carboxylic acid, aldehyde, primary
alcohol
  b. aldehyde, carboxylic acid, primary
alcohol
  c. primary alcohol, aldehyde, carboxylic
  a. hydroxyl; tertiary; secondary acid
  b. hydroxyl; primary; secondary   d. primary alcohol, carboxylic acid,
aldehyde
  c. hydroxyl; secondary; tertiary
  e. aldehyde, primary alcohol, carboxylic
  d. carbonyl; secondary; primary
acid
  e. carboxyl; primary; secondary 40. Which of these functional groups contains a
34. All alcohols contain which functional group? carbon atom doubly bonded to an oxygen atom?
  a. −NH2OH   a. aldehyde
  b. −OH   b. alcohol
  c. −CHO   c. ketone
  d. −CO2H   d. both aldehyde and ketone
  e. −CH2OH   e. both ketone and alcohol
35. Consider the carbon skeleton shown below. To 41. Which of the following compounds is a
form a primary alcohol, the functional group can be dihydroxy alcohol?
bonded to which carbon atom(s)?   a. 2-propanol
  b. 1,2-ethanediol
  c. 1,2,3-propanetriol
  d. ethanol
  e. both 1,2-ethanediol and 1,2,3-
propanetriol
  a. 1, 2, or 7 42. How many of these functional groups contain
  b. 2 or 6 either a carbon atom doubly bonded to an oxygen
  c. 4 atom, a hydrogen atom singly bonded to an oxygen
  d. 3, 5, or 6 atom, or both: alcohol, aldehyde, carboxylic acid,
ketone?
  e. any of them
  a. 2
36. In the first step of oxidation of alcohols, primary
alcohols produce _____, secondary alcohols   b. 4
produce _____, and tertiary alcohols produce   c. 3
_____.   d. 1
  a. no reaction; aldehydes; ketones   e. 0
43. Consider three molecules of similar molecular 50. Which is the correct IUPAC name for the
weight, one a hydrocarbon, another a primary following compound?
alcohol, and the third a carboxylic acid. Arrange the
molecules in order from highest to lowest boiling
point.
  a. hydrocarbon, carboxylic acid, alcohol
  b. carboxylic acid, alcohol, hydrocarbon
  c. hydrocarbon, alcohol, carboxylic acid
  d. alcohol, carboxylic acid, hydrocarbon
  e. carboxylic acid, hydrocarbon, alcohol
44. Which statement concerning carboxylic acids is
incorrect?
  a. Carboxylic acids easily form hydrogen
bonds. 51. What is the correct name of the following
compound?
  b. Carboxylic acids are polar at the
carboxyl group.
  c. Carboxylic acids are produced by
complete oxidation of primary alcohols.
  d. Carboxylic acids react with bases to
form salts.
  e. Carboxylic acids are either primary or
secondary functional groups.
45. Esters are produced by a process which can be
characterized as
52. What is the correct name of the following
  a. a condensation reaction. molecule?
  b. a hydrolysis reaction.
  c. the reaction of alcohols with carboxylic
acids.
  d. both a hydrolysis reaction and the
reaction of alcohols with carboxylic
acids.
  e. both a condensation reaction and the
reaction of alcohols with carboxylic
acids.
46. A hydrolysis reaction is one in which 53. Predict which of the following compounds will
  a. chemical bonds are broken by reaction have a lower boiling point than 1- butanal.
with water and are replaced with −H and a. 1-butanol b. 2-butanol c. 1-butene d. butanoic
−OH. acid
  b. a functional group is moved from one
part of the molecule to another.
  c. an atom or functional group is replaced
by a different atom or functional group.
  d. two molecules combine to form a larger
molecule, splitting out a small molecule.
  e. a small functional group is transferred
from one molecule to another molecule.
47. Saponification involves
  a. the alkaline hydrolysis of an ester.
  b. the hydrolysis of a triglyceride.
  c. the use of an alkaline aqueous solution
as a hydrolytic medium.
  d. the formation of a soap and glycerol.
  e. all of these choices.
48. A strong signal at 1700 cm–1 in an IR spectrum
indicates the presence of a(n)
a. alcohol b. ether c. carbonyl d. amine
49. Which of the following may be separated by
ordinary physical methods?
a. a pair of identical molecules b. a pair of
enantiomers c. a pair of diastereomers d. a pair of
identical atoms