Chemistry 11 (HL)
Unit 7 / IB Topics 10 and 20
Organic Chemistry Review
MULTIPLE CHOICE
1.
What product results from the reaction of CH2CH2 with Br2?
A.
C.
2.
CH2CH2
HCOOCH3
CH2OHCHOHCH2OH
CH3CH2COOH
B.
D.
I and II only
II and III only
B.
D.
CH3COCH3
CH3COOCH3
I. CH3(CH2)2CH3
II. CH3CH(CH3)CH3
III. (CH3)3CH
I and III only
I, II and III
H2NCH2COOH
CH3CHBrI
B.
D.
CH2ClCH2Cl
HCOOCH3
Which reaction(s) involve(s) the formation of a positive ion?
–
I.
CH3CH2CH2Br + OH
–
II.
(CH3)3CBr + OH
A.
C.
7.
B.
D.
Which compound can exist as optical isomers?
A.
C.
6.
CH3CHO
CH3COOH
Which formulas represent butane or its isomer?
A.
C.
5.
CH2CHBr
CH2BrCH2Br
Which of the substances below is least soluble in water?
A.
C.
4.
B.
D.
What is the final product formed when CH3CH2OH is refluxed with acidified potassium
dichromate(VI)?
A.
C.
3.
CHBrCHBr
CH3CH2Br
I only
Both I and II
B.
D.
II only
Neither I nor II
Which compound has the lowest boiling point?
A.
C.
CH3CH2CH(CH3)CH3
CH3CH2CH2CH2CH3
B.
D.
(CH3)4C
CH3CH2OCH2CH3
p. 1
Chemistry 11 (HL)
8.
What type of reaction does the equation below represent?
CH2CH2 + Br2 → BrCH2CH2Br
A.
C.
9.
C.
D.
(CH3)3CCl
(CH3)3CBr
B.
D.
CH3CH2CH2CH2Br
CH3CH2CH2CH2Cl
1-chloropropene
1-bromopropane
B.
D.
1-chlorobutane
1,1-dichloropropane
–
It involves heterolytic fission and Cl ions.
It involves heterolytic fission and Cl• radicals.
–
It involves homolytic fission and Cl ions.
It involves homolytic fission and Cl• radicals.
Which compound is converted to butanal by acidified potassium dichromate(VI) solution?
A.
C.
13.
condensation
addition
Which statement is correct about the reaction between methane and chlorine?
A.
B.
12.
B.
D.
Which compound is a member of the same homologous series as 1-chloropropane?
A.
C.
11.
substitution
reduction
Which compound reacts most rapidly by a SN1 mechanism?
A.
C.
10.
Unit 7 / IB Topics 10 and 20
butan-1-ol
butanone
B.
D.
butan-2-ol
butanoic acid
Which pair of compounds can be used to prepare CH3COOCH3?
A.
B.
C.
D.
Ethanol and methanoic acid
Methanol and ethanoic acid
Ethanol and ethanoic acid
Methanol and methanoic acid
p. 2
Chemistry 11 (HL)
14.
Unit 7 / IB Topics 10 and 20
The following is a three-dimensional representation of an organic molecule.
Which statement is correct?
A.
B.
C.
D.
The correct IUPAC name of the molecule is 2-methylpentane.
All the bond angles will be approximately 90°.
One isomer of this molecule is pentane.
The boiling point of this compound would be higher than that of pentane.
SHORT ANSWERS AND PROBLEM SOLVING
1.
Complete the following reactions by naming the product(s) and showing complete structural
formulas for any organic product.
a)
CH3 – CH2 – OH + acidified K2Cr2O7 (heated under reflux) →
b)
C3H6 + Cl2 →
c)
C2H4 + H2O + catalyst at high temperatures →
d)
CH3 – OH + CH3COOH (+ conc. H2SO4) →
e)
C4H10 + O2 (excess) →
f)
CH3Cl + dilute KOH →
g)
C2H4 + hydrogen gas, catalyst, high pressure & heat →
h)
CH3CH2Br + NH3 (in a sealed flask) →
p. 3
Chemistry 11 (HL)
Unit 7 / IB Topics 10 and 20
i)
CH3CH2CN + H2 + nickel catalyst →
j)
CH3 – OH + O2 (limiting) →
2.
a)
How many different structural isomers can you build for dichlorobenzene? Draw
and name all of these possible structural isomers.
3.
Starting with the molecule 2-bromobut-2-ene draw and name the following isomers (if
possible).
a)
b)
c)
d)
e)
a hydrocarbon chain isomer
a functional group isomer
a positional isomer
a geometric isomer
an enantiomer
4.
Define the term racemic mixture.
5.
a) You are given an alkane and an alkene, but you don’t know which is which.
Describe a simple test to be able to differentiate the two.
b)
Distinguish between the reactions of butane and but-2-ene with chlorine.
p. 4
Chemistry 11 (HL)
6.
Unit 7 / IB Topics 10 and 20
Consider the following 3 organic molecules:
H
|
H2N – C – COOH
|
R1
H
|
H2N – C – COOH
|
R2
H
|
H2N – C – COOH
|
R3
a)
What type of reaction would be required to combines the 3 together?
b)
Show the product(s) of this reaction.
7.
What is a tertiary alcohol? Provide an example and name the alcohol.
8.
You are given 2 samples of citric acid. The first is made naturally by citrus fruit and the
second is made synthetically in the laboratory. How could you tell the 2 apart? (2)
9.
Explain, at a molecular level, why ethanol is soluble in water, but cholesterol (C27H45OH) is not.
10. Give the balanced equation for the complete combustion of propane. Identify two
products
formed form an incomplete combustion of propane and identify one harmful effect caused by
one of these byproducts.
11. The molecule below contains 2 important functional groups:
CH3 COOH
\
/
C=C
/
\
CH3 H
a)
Circle and name the 2 functional groups.
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Chemistry 11 (HL)
Unit 7 / IB Topics 10 and 20
b)
For each functional group present in the above molecule, give 1 chemical reaction
that could be carried out and the result that would indicate the presence of this
group.
c)
Is this an example of a geometric isomer? Explain why or why not.
12. Explain the term condensation and state the structural features of the monomers required to form
condensation polymers. How does addition polymerization differ from condensation
polymerization?
13. Tyrelene® is a polymer produced from the polymerization of the two monomers
ethane-1,2-diol and benzene-1,4-dicarboxylic acid. State the type of polymer that Tyrelene® is
and draw the structural formula for the repeating unit.
14. a)
b)
Draw the structures of 2-chloropropanoic acid and 2-hydroxypropanoic acid.
2-chloropropanoic acid can be converted to 2-hydroxypropanoic acid by nucleophilic
substitution. Define the term nucleophile and state the nucleophile required for this reaction.
Show how this mechanism might proceed by an SN1 mechanism.
p. 6
Chemistry 11 (HL)
Unit 7 / IB Topics 10 and 20
14. 2-chloropropane can be converted to 1-propanol by an SN2 mechanism.
a)
Define the acronym SN2. (1)
b)
Draw the mechanism. (3)
15. Compare and explain the relative boiling points of these compounds:
a)
A = CH3CH2COOH
B = CH3COOCH3
b)
X = CH3CH2CH2CH2CH3
c)
the two enantiomers of 2-chloro-2-methylbutane
C = CH3CH2CH2CHO
Y = CH3C(CH2)2CH3
16. Reaction Pathways – How would you produce the following?
*Write the balanced equation for each step, including conditions.
*Name all reactants and products.
a)
ethanoic acid starting with a haloalkane
b)
1,2 – dichloro-2-pentene with an alkane.
c)
ethanal from an alkene.
p. 7
Chemistry 11 (HL)
17.
Unit 7 / IB Topics 10 and 20
d)
butanamide starting with a haloalkane and an alcohol. OMIT
e)
methylpropanoate starting from butanol propanol and methane.
a)
b)
Identify the formulas of the organic products, A–E, formed in the reactions, I–IV:
I.
CH3(CH2)8OH + K2Cr2O7
II.
(CH3)3CBr + NaOH
III.
(CH3)2CHOH + K2Cr2O7
IV.
H2C=CH2 + Br2
C
D
E
H2C=CH2 can react to form a polymer. Name this type of polymer and draw the
structural formula of a section of this polymer consisting of three repeating units.
p. 8