Organic Unit Test
23
K/U 12
Comm 12
App Name __________________ 8
T/I Part A: Multiple Choice
Identify the choice that best completes the statement or answers the question. (10 marks) 1. How many isomers are there with the formula C3H5Br? Include both structural and goemetric
isomers.
a) 2
d) 5
b) 3
e) 6
c) 4
2. Which of the following will yield a carboxylic acid upon oxidation?
a) a secondary alcohol
d) a ketone
b) an aldehyde
e) a tertiary alcohol
c) a cycloalkane
3. For which of the following compound(s) are cis and trans isomers possible?
a) 2,3-dimethyl-2-butene
d) 1,3,5-trichlorobenzene
b) 3-methyl-2-pentene
e) all can exhibit cis/trans isomersism
c) 1-chloro-4-methyl-2-pentyne
4. When both hydrogens of water are replaced by alkyl groups, the compound becomes:
a) an aldehyde
d) a secondary alcohol
b) a ketone
e) a carboxylic acid
c) an ether
5. Which one of the following acyclic compounds is a member of the alkyne family?
a) C3H6
d) C6H10
b) C4H8
e) C5H12
c) C7H14
6. 2-propanol is a :
a) primary alcohol
b) secondary alcohol
c) tertiary alcohol d) ketone
e) ether 7. Which one of the following acyclic compounds is unsaturated?
a) C6H14
d) CH4
b) C4H8
e) C2H6
c) C3H8 8. The general formula for a cyclic alkane is:
a) C2nHn
b) CnHn
c) CnH2n+2 d) CnH2n
e) CnH2n-2 9. Which of the following is an isomer of 2-butene?
a) 2-methylpropane
b) cyclobutene
c) 2-methylbutene d) methylcyclopropane
e) 1,3-dimethylpropane 10. Cis-trans isomers are possible because of:
a) free rotation about a single bond
b) carbon bonding orbitals are tetrahedral
c) there is no rotation about single bonded carbons
d) there is no rotation about double bonded carbons
e) organic molecules can resonate Part B: Short Answer
Answer all of the questions in the space provided. Marks for each question are indicated.
1. Give the proper IUPAC name for the following
a) (2 marks) b) (3 marks) CH3 CH3 CH
H3C c) CH2 H2C C CH3 H3C (3 marks) d) CH3 CH
C CH2 CH3 CH3 (3 marks) O OH H3C e) (2 marks) CH2
H3C CH2 O
CH2 C
CH2 O CH2
CH2 CH3 CH3
CH2 2. Explain why the following names are wrong according to IUPAC .
a) 2-methyl-3-chloro-3-butene b) cis 3-bromo-5-ethyl-1-hexyne (2 marks) (2 marks) 3. Draw the following structures. ( 8 marks)
a) 2-methylheptanal c) 1,4-diaminobutane b) 1-bromobenzene d) 2-chloropentanoic acid 4. Fill in ALL of the missing components to make the reaction complete. Draw STRUCTURAL diagrams
where possible. Do NOT balance. Naming of the compounds is NOT necessary. (12 marks)
a) b) Br2 + heat CH2
H3C CH3 c) 2-methyl butane d) + OXYGEN + F-F + Strong H2SO4 2-butene + H2O O e) CH3OH + + H2O
CH2
H3C f) 2-propanone + Heat, Pressure, H2 ,Pt C
CH2 CH3
O 5. Please choose ONE of the following questions. ONLY complete the question you are most confident. A compound of formula C3H8O exists as two isomers, A and B. With a catalyst and KMnO4 (which is a
strong oxidizing agent), compound A forms another compound, C of formula C3H6O, while B forms
compound D of formula C3H6O2. A simple litmus test reveals that compound D is a weak acid. Give the
IUPAC names AND draw the structures of the four compounds. (8 marks) OR
Explain in detail how to synthesize 1-chloropropanone from 1-chloropropane. Include all structural diagrams
and IUPAC names of reactants and Organic Unit Test

23
K/U 12
Comm 12
App Name __________________ 8
T/I Part A: Multiple Choice
Identify the choice that best completes the statement or answers the question. (10 marks) 1. How many isomers are there with the formula C3H5Br? Include both structural and goemetric
isomers.
a) 2
d) 5
b) 3
e) 6
c) 4
2. Which of the following will yield a carboxylic acid upon oxidation?
a) a secondary alcohol
d) a ketone
b) an aldehyde
e) a tertiary alcohol
c) a cycloalkane
3. For which of the following compound(s) are cis and trans isomers possible?
a) 2,3-dimethyl-2-butene
d) 1,3,5-trichlorobenzene
b) 3-methyl-2-pentene
e) all can exhibit cis/trans isomersism
c) 1-chloro-4-methyl-2-pentyne
4. When both hydrogens of water are replaced by alkyl groups, the compound becomes:
a) an aldehyde
d) a secondary alcohol
b) a ketone
e) a carboxylic acid
c) an ether
5. Which one of the following acyclic compounds is a member of the alkyne family?
a) C3H6
d) C6H10
b) C4H8
e) C5H12
c) C7H14
6. 2-propanol is a :
a) primary alcohol
b) secondary alcohol
c) tertiary alcohol d) ketone
e) ether 7. Which one of the following acyclic compounds is unsaturated?
a) C6H14
d) CH4
b) C4H8
e) C2H6
c) C3H8 8. The general formula for a cyclic alkane is:
a) C2nHn
b) CnHn
c) CnH2n+2 d) CnH2n
e) CnH2n-2 9. Which of the following is an isomer of 2-butene?
a) 2-methylpropane
b) cyclobutene
c) 2-methylbutene d) methylcyclopropane
e) 1,3-dimethylpropane 10. Cis-trans isomers are possible because of:
a) free rotation about a single bond
b) carbon bonding orbitals are tetrahedral
c) there is no rotation about single bonded carbons
d) there is no rotation about double bonded carbons
e) organic molecules can resonate Part B: Short Answer
Answer all of the questions in the space provided. Marks for each question are indicated.
1. Give the proper IUPAC name for the following
a) (2 marks) b) (3 marks) CH3 CH3 CH
H3C c) CH2 H2C C CH3 H3C (3 marks) d) CH3 CH
C CH2 CH3 CH3 (3 marks) O OH H3C e) (2 marks) CH2
H3C CH2 O
CH2 C
CH2 O CH2
CH2 CH3 CH3
CH2 2. Explain why the following names are wrong according to IUPAC .
a) 2-methyl-3-chloro-3-butene b) cis 3-bromo-5-ethyl-1-hexyne (2 marks) (2 marks) 3. Draw the following structures. ( 8 marks)
a) 2-methylheptanal c) 1,4-diaminobutane b) 1-bromobenzene d) 2-chloropentanoic acid 4. Fill in ALL of the missing components to make the reaction complete. Draw STRUCTURAL diagrams
where possible. Do NOT balance. Naming of the compounds is NOT necessary. (12 marks)
a) b) Br2 + heat CH2
H3C CH3 c) 2-methyl butane d) + OXYGEN + F-F + Strong H2SO4 2-butene + H2O O e) CH3OH + + H2O
CH2
H3C f) 2-propanone + Heat, Pressure, H2 ,Pt C
CH2 CH3
O 5. Please choose ONE of the following questions. ONLY complete the question you are most confident. A compound of formula C3H8O exists as two isomers, A and B. With a catalyst and KMnO4 (which is a
strong oxidizing agent), compound A forms another compound, C of formula C3H6O, while B forms
compound D of formula C3H6O2. A simple litmus test reveals that compound D is a weak acid. Give the
IUPAC names AND draw the structures of the four compounds. (8 marks) OR
Explain in detail how to synthesize 1-chloropropanone from 1-chloropropane. Include all structural diagrams
and IUPAC names of reactants and products to illustrate your answer. (8 marks)

products to illustrate your answer. (8 marks)

 

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