SCH4U - U6 Organic Chemistry

1. Carbon is able to form large numbers of organic compounds because carbon can 

a.	form 4 bonds.	d.	the carbon-carbon bond is very stable.
b.	form single, double and triple bonds.	e.	All of a), b), c) and d).
c.	form chains, rings, spheres and sheets.

e.	All of a), b), c) and d).

2. Which compound(s) cannot be classified with organic compounds?

a.	carbohydrates and sugars	d.	graphite
b.	fats and protein	e.	none of the above
c.	polyester, wool, and cotton

d.

graphite

3. What is the general formula for alkenes?

a.CnHn+2

b.CnH2n+2

c.CnH2n

d.CnH2n-2

e.CnHn-2

c.C_nH_2n 

4. Which compound is a constitutional isomer of the compound shown below?

 

a.propane

b.butane

c.methane

d.pentane

e.hexane

d.pentane

5. Isomers in which molecules form mirror images of each other around a carbon atom are _____________.

a.	enantiomers	d.	structural isomers
b.	diastereomers	e.	none of the above
c.	constitutional isomers

a.	enantiomers

6. Which one of the molecules below has a chiral (optical) isomer?

c.

7. Which hydrocarbon does this diagram represent?

 

a.	pentane	c.	heptane	e.	decane
b.	methylheptane	d.	octane

d.

octane

8. What is the IUPAC name of the following compound?

 

a.	pentanoic acid	c.	propyl methanoate	e.	3-methylbutanol
b.	butanoic acid	d.	2 – oxy butan-1-ol

b.	butanoic acid

9. What is the IUPAC name of the following molecule?

 

a.	1, 2-dichlorobenzene	c.	1, 5-dibenzochloride	e.	1, 5-dichlorobenzene
b.	1, 3-dichlorobenzene	d.	1, 3-dibenzochloride

b.	1, 3-dichlorobenzene

10. Which of the following molecular structures represents 1,3-dimethylcyclobutane?

a.

b.

c.

d.

11. Ethylene glycol acts as antifreeze and is used in automobiles and computers. It is also used for preserving body organs and in the manufacture of capacitors. Its structure is shown below.

 

The IUPAC name of this compound is

a.	ethanol	d.	2,2-dihydroxyethane-1,2-diol
b.	ethane-1,2-diol	e.	diethane-1,2-diol
c.	1-hydroxyethane-1,2-diol

b.	ethane-1,2-diol

12. What is the correct name for the compound?

 

a.	2-methyl-3-butanol	d.	3-methyl-2-butanol
b.	2-pentanol	e.	none of these
c.	isobutanol

d.	3-methyl-2-butanol

13. This fruit-scented compound is generally used in ice creams and other food stuffs as a flavouring agent. The IUPAC name of the compound is

 

a.	propyl ethanoate	c.	ethyl propanoate	e.	methyl propanoate
b.	propane ethanoate	d.	ethane propanoate

c.	ethyl propanoate

14. The IUPAC name of this compound is

 

a.non-5-yne

b.hept-3-yne

c.oct-4-yne

d.dec-5-yne

e.hex-4-yne

d.dec-5-yne

15. What is the IUPAC name for the following compound?

 

a.2-ethoxypropene

b.2-ethoxypropane

c.2-methoxyethene

d.2-methoxyethane

b.2-ethoxypropane

16. What is the other name for methoxymethane?

a.2-methoxyethane

b.toluene

c.methyl alcohol

d.dimethyl ether

d.dimethyl ether 

17. What is the name of the following molecule?

 

a.toluene-1,2-diol

b.hexen-1,6-diol

c.1,2-dihydroxybenzene

d.none of the above

c.1,2-dihydroxybenzene

18. What is the IUPAC name for the following compound? 

 

a.	3-propylbutanoic acid	c.	4-methylhexanoic acid
b.	3-methylhexanoic acid	d.	4-propylbutanoic acid

b.	3-methylhexanoic acid

19. What is the structure of N-methylpentan-2-amine?

a.	c.
b.	d.

c.

20. The correct name for the compound given is which of the following?

 

a.	2-methyl-1-butene	c.	2-ethyl-1-propene	e.	2-ethyl-1-pentene
b.	pentene	d.	3-methyl-2-butene

a.	2-methyl-1-butene

21. The correct name for compound shown is which of the following?

 

a.	chloropropylbenzene	c.	1-chloro-3-phenyl-3-propene
b.	3-phenyl-1-choloropropyne	d.	3-chloro-1-phenyl-1-propene

d.	3-chloro-1-phenyl-1-propene

22. What is the proper name for the structure given below?

 

a.	3-methyl-2-butanone	c.	1-ethyl-1-propanone
b.	3-pentanone	d.	1,1-dimethyl-1-propanone

a.	3-methyl-2-butanone

23. The correct name for the compound given  is which of the following?

 

a.	3-amino-3-hexanone	c.	N-propylpropanamide
b.	ethyl ethanamide	d.	N-ethylethanamide

c.	N-propylpropanamide

24. The correct IUPAC name for the following structure is

 

a.	4,4-diethylheptanal	c.	3-ethal-3-propylpentane
b.	3-ethyl-3-ethonehexane	d.	3,3-diethylhexanal

d.	3,3-diethylhexanal

25. Which of the following is paradichlorobenzene?

a.

b.

c.

d.

b.

26. How many functional groups are there in this compound?

 

a.One

b.Two

c.Three

d.Four

e.Five

b.Two

27. Which functional group does the compound CH₃CH₂NHCH(CH₃)₂ possess?

a.	aldehyde	c.	carboxylic acid	e.	alkyne
b.	amine	d.	ether

b.

amine

28. What type of compound is the following structure?

 

a.	ether	c.	ester	e.	amide
b.	alcohol	d.	carboxylic acid

c.

ester

29. A carboxyl group is always ____________________.

a.	at the end of a chain	d.	on either side of a chain
b.	at the beginning of a chain	e.	anywhere on the chain
c.	in the middle of a chain

a.	at the end of a chain

30. Sodium benzoate is widely used as a preservative in food. Sodium benzoate is a(n) _______.

a.	ester	c.	amide	e.	alcohol
b.	amide	d.	carboxylic acid

a.

ester

31. Which of the following carboxylic acids is the least soluble in water?

a.	CH3 COOH	c.	C3H7COOH	e.	HCO2H
b.	C2 H5COOH	d.	C4 H9 COOH

d.	C4 H9 COOH

32. Why does the boiling point of an alkane increase as its chain length increases?

    a.	There is more hydrogen bonding.
    b.	There are hydrogen atoms available for hydrogen bonds to form.
    c.	The molecules are highly branched.
    d.	The strength of the dispersion forces increases with increased molecular size.
    e.	None of the above are correct.

c.	The molecules are highly branched.

33. Which of the following compounds has the lowest boiling point?

a.	pentane	c.	2-methylpentane
b.	2,2-dimethylpropane	d.	hexane

b.	2,2-dimethylpropane

34. The boiling points of alkanes and their associated substituted hydrocarbons can be compared. Differences are explained mostly by polarity and intermolecular forces. Assuming each compound has the same number of C atoms in the base chain, which is the correct arrangement in order from lowest boiling point to highest boiling point?

lowest b.p.---->---------------->---------------->---------------->---------------->----highest b.p
i)     alkane	alcohol	carbonyl	amide	carboxylic acid
ii)    alkane	carbonyl	alcohol	carboxylic acid	amide
ii)    amide	carbonyl	carboxylic acid	alcohol	alkane
iv)   carbonyl	alcohol	carboxylic acid	amide	alkane

a.i) is correct.

b.ii) is correct.

c.iii) is correct.

d.iv) is correct.

b.ii) is correct.

ii)    alkane

carbonyl

alcohol

carboxylic acid

amide

35. Which statement is INCORRECT concerning these two molecules with the same formula, C₂H₆O?

a.	Compound (II) will more likely be soluble in water than compound (I).
b.	Compound (I) will have a lower boiling point than compound (II).
c.	Hydrogen bonding will be the most likely for compound (II).
d.	Compound (II) will evaporate at a faster rate than that of compound (I) at a given temperature.

d.	Compound (II) will evaporate at a faster rate than that of compound (I) at a given temperature.

36. Reaction i) is an example of a 

a.	elimination	c.	substitution	e.	hydrolysis
b.	addition	d.	condensation	f.	oxidation

b.

addition

37. Reaction ii) is an example of a 

a.	elimination	c.	substitution	e.	hydrolysis
b.	addition	d.	condensation	f.	oxidation

f.

oxidation

38. Reaction iii) is an example of a 

a.	elimination	c.	substitution	e.	hydrolysis
b.	addition	d.	condensation	f.	oxidation

b.

addition

39. Reaction iv) is an example of a 

a.	elimination	c.	substitution	e.	hydrolysis
b.	addition	d.	condensation	f.	oxidation

e.	hydrolysis

40. In reaction iii), the product is

a.	propyl butanoate.	c.	propyl propanoate.	e.	None of a), b), c) or d).
b.	ethyl propanoate.	d.	butyl propanoate.

c.	propyl propanoate.

41. In the presence of UV light, the following reaction occurred:

CH₄ + Cl₂ ---> CH₃Cl + HCl

What type of reaction does this represent?

a.	esterification	c.	hydrolysis	e.	elimination
b.	substitution	d.	addition

b.	substitution

42. Which of these is NOT true regarding elimination reactions?

a.	They can be thought of as the reverse of an addition reaction.
b.	Atoms are removed from an organic molecule to form a double bond.
c.	Carbon atoms in the organic product are bonded to more atoms than were the carbon atoms in the organic reactant.
d.	Alcohols can undergo elimination reactions to form alkenes.
e.	Haloalkanes can undergo elimination reactions to form alkenes.

c.	Carbon atoms in the organic product are bonded to more atoms than were the carbon atoms in the organic reactant.

43. Which of these does NOT occur in a substitution reaction?

a.	two compounds react to form two different compounds
b.	carbon atoms are bonded to a different number of atoms in the product than in the reactant
c.	a hydrogen atom or functional group is replaced by a different atom or functional group
d.	aromatic hydrocarbons will undergo substitution reactions with chlorine and bromine in the presence of a catalyst
e.	a haloalkane can undergo a substitution reaction with a hydroxide ion to produce an alcohol

b.	carbon atoms are bonded to a different number of atoms in the product than in the reactant

44. The synthesis sequence shown here is best described as which of the following?

 

a.	(1) Dehydration; (2) halogenation; (3) hydrogenation
b.	(1) Hydrogenation; (2) dehydration; (3) halogenation
c.	(1) Hydrogenation; (2) halogenation; (3) dehydration
d.	(1) Halogenation; (2) hydrogenation; (3) dehydration
e.	(1) Dehydration; (2) hydrogenation; (3) halogenation

e.	(1) Dehydration; (2) hydrogenation; (3) halogenation

45. In a hydration reaction, an alkene is converted to what type of compound?

a.an amide

b.an alkyne

c.an alcohol

d.an aldehyde

c.an alcohol

46. When two alcohols undergo a condensation, what is formed?

a.	liquid alcohol	c.	an ester	e.	an ether
b.	a ketone	d.	an aldehyde

e.

an ether

47. Which reaction is the “reverse” of a condensation reaction?

a.	esterification	c.	addition	e.	oxidation
b.	hydrolysis	d.	substitution

b.	hydrolysis

48. The reaction below is catalized by H₂SO₄.

CH₃COOH + CH₃CH₂OH ----> CH₃COOCH₂CH₃ + H₂O

As well as being a dehydration synthesis, which reaction does this represent?

a.	esterification	c.	addition	e.	elimination
b.	hydrolysis	d.	oxidation

a.	esterification

49. When propene is treated with bromine water, Br₂(l), in the presence of carbon tetrachloride as a catalyst, the product is:

a.	1,2–dibromopropane	c.	2–bromopropane	e.	none of these
b.	2,2–dibromopropane	d.	1–bromopropane

a.	1,2–dibromopropane

50. In an oxidation reaction, a carbon atom forms  ___i___ bonds to oxygen atoms or ___ii___ bonds to hydrogen atoms. The statement given above is completed by the information in row 

Row	i	ii
A	more	the same
B	more	fewer
C	fewer	more
D	fewer	the same
E	fewer	fewer

a.

b.

c.

d.

e.

b.

B

more

fewer

51. In a chemical equation, the symbol [O] represents _____________.

a.	an oxidizing agent	d.	catalysis by a strong acid
b.	a reducing agent	e.	the presence of a base
c.	an oxygen molecule

a.	an oxidizing agent

52. Which reactions can be used to characterize addition polymerization?

a.	addition	c.	substitution	e.	substitution
b.	oxidation	d.	condensation

a.

addition

53. Nylons are condensation polymers with _________ .

a.	amide linkages	c.	amine linkages	e.	alpha linkages
b.	ester linkages	d.	beta linkages

a.	amide linkages

54. Many polymers are more familiarly known by there common names (such as polypropylene), acronyms (such as PVC), or by their patented names (as in Kevlar). The polymerization of which monomer produces PVC?

a.	chloroethene	c.	ester	e.	acrylamide
b.	styrene	d.	glucose

a.	chloroethene

55. A copolymer is a polymer in which

a.	all of the monomers are identical.
b.	there are two or more different monomers.
c.	the monomers are held together only by ionic bonds.
d.	there is cross-linking between molecules.

b.	there are two or more different monomers.

56. Identify the shorthand notation for the following polymer.

d.

57. What is the monomer of the following polymer?

c,

____ 58. The properties of which of the following makes them excellent substances for making formed products? 

a.	natural polymers	c.	copolymers	e.	thermoplastic polymers
b.	addition polymers	d.	condensation polymers

e.	thermoplastic polymers

Matching:

59. Aldehydes

60. Ether             

61. alkenes

62. amines 

63. amides

64. thiols

65. alkyl halides

66. ketones

67.  ester

68.  alcohols

59. H

60. E

61. F

62. D

63. B

64. J

65. C

66. G

67. I

68. A

69. Ethane serves as the parent chain for several  common organic compounds.  Write the structural formulas and give the IUPAC name for the alcohol, the aldehyde, and the carboxylic acid derivatives of ethane. (3 marks)

Bonus (upto 3 marks): Give the common names.

	alcohol	aldehyde	carb. acid
structural formula
IUPAC name

1.alchohol: CH₃CH₂OH  ethanol  alchohol/booze 

aldehyde: CH₃CH₂O ethanal acetaldehyde

carboxylic acid: CH₃CHOOH ethanoic acid acetic acid/vinegar

70. Why is 2-ethyl octane NOT an acceptable IUPAC name for the structure provided? Explain and provide the correct IUPAC name for the structure. (2 marks)

because it does not take into account the longest chain for the molecule. The proper name is 3-methyl nonane.       

71. The common name for this strucure might be Spot. 

a) On the diagram, circle the substituent groups and name them.  Do the same for the base chain. (2 marks)

b) Give the systematic name.  (2 marks)

B) 3,5,5-triethyl-3-phenylheptane

72. An addition reaction occurs between but-1-ene and hydrochloric acid.  Give the structural diagram for the reaction and both possible products, and indicate which product should be the major one. (4 marks)

73. Draw the structural formula for the following compounds. For C-H, show only the C- (omit the H atoms). (4 marks)

(a) butanoic acid

(b) 1,3-dibromopentane 

(c) 3-isopropylhex-1-ene

(d) cis-pent-2-ene

74. When a hydrocarbon burns in an excess of oxygen, it produces carbon dioxide and water. Write the balanced chemical equation for the complete combustion of pentene. (2 marks)

2C₅H₁₀(g) + 15O₂(g) → 10CO₂(g) + 10H₂O(g)   

b) incomplete combustion: products such as CO or C form in addition to water and carbon dioxide    

-water gets first crack at the oxygens

75. Organic chemists tend to look at redox reactions in terms of oxygen and hydrogen and the localized electron density around the carbon backbone.  Explain how an oxidation reaction is different from a reduction reaction. (3 marks)

In organic chemistry, an oxidation reaction occurs when a carbon atom forms more bonds to oxygen or fewer bonds to hydrogen. This means the carbon becomes more electron-deficient. In contrast, a reduction reaction takes place when a carbon atom forms fewer bonds to oxygen or more bonds to hydrogen, increasing the electron density around the carbon. Organic chemists focus on these changes in bonding and electron density to track redox processes in carbon-based molecules.

76.

a) Differentiate between an addition polymerization and a condensation polymerization.(2 marks)

b) Kevlar, a strong polymer used in bulletproof vests, is made by the condensation of two monomers: 

  and  

Draw the structure of one subunit of the Kevlar polymer. (2 marks)

c) F₂C=CF₂ is used to produce the polymer commonly know as Teflon.  What kind of polymerization reaction occurs and what is the IUPAC name of the polymer? (2 marks)

a) Addition polymerization is a process where monomers containing carbon-carbon double bonds (C=C) react to form long polymer chains. The double bonds break, and the monomers link together without producing any by-products.

Condensation polymerization involves monomers with two functional groups (such as –COOH and –NH₂ or –OH) that react to form covalent bonds (typically ester or amide bonds). During each bond formation, a small molecule like water (H₂O) is released — this is often a dehydration reaction.
These polymers are typically copolymers, formed from two or more different types of monomers.

c)

An addition polymerization reaction occurs because the monomer F₂C=CF₂ (tetrafluoroethene) contains a carbon–carbon double bond. During the reaction, these double bonds open up and link together to form a long chain, without producing any by-products.

The IUPAC name of the polymer formed is polytetrafluoroethene.

77. Propene (common name propene) is the basis of various polymers used in textiles (fabrics).

a) Draw the structural diagram for the monomer and a section of the polymer with three monomer subunits. (3 marks)

b) Tacticity refers to the arrangement of the substituent groups along the molecule: isotactic, syntactic and atactic polymers exist.  Complete the drawing using 3D wedges to show the isotactic form of the polymer. (2 marks)

C-C=C ,   b) all on the same plane c )intermolecular bonding: isotactic bond is better, atactic poorest

78. There are 20 common amino acids that can be combined in an extraordinary number of combinations to make up all the proteins that are necessary for biological functions in living organisms. Using the generic backbone to the 20 common amino acids, draw a protein that is three amino acids long and identify the functional groups on amino acids. (4 marks)

All 20 amino acids have a carboxyl group (-COOH) and an amino group (-NH₂), with a different R group, giving them their distinct properties

that should say amide bond