Download Organic Chemistry Questions

Organic
The Advanced Placement Examination in Chemistry
Part I – Multiple Choice Questions
Part II – Free Response Questions
Part III – Equations
Selected Questions from1970 to 2010
Organic Chemistry
Part I
1984
77. Which of the following compounds exhibits optical isomerism?
(A)
(B)
(C)
(D)
(E)
1994
43. Which of the following pairs of compounds are isomers?
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1994
29. The organic compound represented above is an example of
(A) an organic acid
(B) an alcohol
(C) an ether
(D) an aldehyde
(E) a ketone
2002
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2008
61. The structure of a molecule of “banana oil” is shown above. This organic compound is an example
of
(A) an alcohol
(B) an amine
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(C) a carboxylic acid
(D) an ester
(E) a ketone
70. Naturally produced amino acids typically contain all of the following elements EXCEPT
(A) nitrogen
(B) chlorine
(C) oxygen
(D) hydrogen
(E) carbon
Part II
1972
What types of isomerism are possible among the molecules that can be obtained by substituting a
chlorine atom and a bromine atom for two of the hydrogen atoms in each of the following?
(a) Ethane, C2H6
(b) Ethene, C2H4
Show structures to illustrate each of the types of isomerism you name for each of these compounds.
1975
Draw structural formulas for seven different isomers of C3H4Cl2.
1977
Write structural formulas for two stable isomers X and Y that have the molecular formula C 2H4O2. Select
a physical property and a chemical property that would distinguish between the two isomers in the
laboratory. Explain.
1978
Dehydration of 3-hexanol yields a mixture of four isomers each with the molecular formula C6H12. Draw
structures of the four isomers and name each of them.
1981
Assume that you have two different gases that you know are not cyclic (i.e. not ring) compounds, each
with the following elementary analysis: C = 85.7%, H = 14.3%. Each gas has a molecular weight of 56 ±
1.
(a) What is the molecular formula for the compounds?
(b) Draw the structural formulas for the four possible noncyclic isomers with this molecular formula.
(c) In the presence of an appropriate catalyst, both gases add hydrogen. The hydrogenated products are
identical, their molecular weight is 58. Which of the structures you drew to answer (b) can definitely
be eliminated on the basis of this additional information?
1998
Answer each the following using appropriate chemical principles.
Dimethyl ether, H3C–O–CH3, is not very soluble in water. Draw a structural isomer of dimethyl ether that
is much more soluble in water and explain the basis of its increased water solubility.
In each case, justify your choice.
2002
Consider the hydrocarbon pentane, C5H12 (molar mass 72.15 g).
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The structural formula of one isomer of pentane is shown below. Draw the structural formulas for the
other two isomers of pentane. Be sure to include all atoms of hydrogen and carbon in your structures.
2003
Compound
Name
Compound
Formula
∆H˚vap
(kJ mol-1)
Propane
CH3CH2CH3
19.0
Propanone
CH3COCH3
32.0
1-propanol
CH3CH2CH2OH
47.3
Using the information in the table above, answer the following questions about organic compounds.
(a) For propanone,
(i)
draw the complete structural formula (showing all atoms and bonds);
(ii) predict the approximate carbon-to-carbon-to-carbon bond angle.
(b) Draw the complete structural formula for an isomer of the molecule you drew in, part (a) (i).
Part III
1971: propene gas is mixed with bromine vapor
1972: a limited amount of liquid bromine is added to an excess of benzene
1973: pure methyl alcohol and pure acetic acid are mixed
1974: a sample of pure 2-butene is treated with hydrogen bromide gas
1975: an excess of chlorine gas is added to pure acetylene
1976: ethyl acetate is treated with a solution of sodium hydroxide
1977: benzene is treated with bromine in the presence of a catalyst
1978: propene reacts with water in the presence of a catalyst
1982: methane gas is heated with an excess of chlorine gas
1985: ethanol and formic acid (methanoic acid) are mixed and warmed
1986: ethene (ethylene) gas is bubbled through a solution of bromine
1987: propanol is burned completely in air
1995: ethanol is burned in oxygen
1998: ethene gas is burned in air
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2000: butanol is burned in air
2001: solutions of potassium hydroxide and propanoic acid are mixed
2004: dimethyl ether is burned in air
2005: ethyne (acetylene) is burned in air
2010 (format change)
Propane is burned completely in excess of oxygen gas.
(i)
Balanced equation:
(ii) When the products of the reaction are bubbled through distilled water, is the resulting solution
neutral, acidic, or basic? Explain.
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