SCH 4U Unit #2 Test – Organic Chemistry

Name: / K/U: /35 / A: /35 / C:

Aids Permitted: ALCHEM Periodic Table, Organic Reactions Flow Chart

Part A – Knowledge and Understanding [35 marks]

Multiple Choice [13]

1.  Organic chemistry is best described as the study of

a) hydrogen-containing compounds c) carbon-containing compounds

b) nitrogen-containing compounds d) oxygen-containing compounds

2.  Which of the following is an unsaturated molecule?

a) C5H8 b) C5H10 c) C5H12 d) a and b are unsaturated

3.  The H-C-C bond angles in ethene are

a) 90⁰ b) 109.5⁰ c) 120⁰ d) 180⁰

4.  Cycloalkenes are isomers of

a) alkynes b) alkenes c) alkanes d) cycloalkanes

5.  Which family of organic compounds has the general formula CnH2nO?

a) alcohols b) aldehydes c) esters d) all of these

6.  The common name for propanone is

a) formaldehyde b) rubbing alcohol c) polypropylene d) acetone

7.  The IUPAC name for toluene is

a) methylbenzene b) phenol c) nitrobenzene d) ethanoic acid

8.  The hydroxyl functional group is found in which family of organic compounds?

a) aldehydes b) carboxylic acids c) aromatics d) alcohols

9.  Which family of organic compounds does not feature a double bond in its functional group?

a) alkenes b) aromatics c) ethers d) amides

10.  The branch name “nitro-“ can be represented by the formula

a) N-- b) NH2-- c) CON-- d) NO2--

11.  3-methyl-2-butanol is an example of a ______alcohol.

a) primary b) secondary c) tertiary d) quaternary

12.  The general formula for the ether family is

a) CnH2nO b) CnH2nO2 c) CnH2n+2O d) CnH2n+2O2

13.  Which organic family is represented by the formula CH3COOCH3?

a) alcohol b) ester c) ketone d) carboxylic acid

Short Answer [22]

14.  Compare and contrast these terms: propane, n-propyl, and i-propyl. [4]

propane / n-propyl / i- propyl
Similarity
Difference

15.  Compare and contrast an amine with an amide. [3]

Amine / Amide
Similarity
Difference

16.  Determine why each IUPAC name listed is incorrect for the structure it represents and, without changing the structure of the molecule, write the correct IUPAC name. [6]

Given name / What is wrong with the name / Correct IUPAC name
2-butyl-2-chloro-2-methylethane
cis-3-ethyl-3-hexene
methyl ethyl pentanamide

17.  Using the formula C8H16, draw a molecule that

a) has two alkyl branches b) is cyclic with one branch [1] c) is a trans isomer [1]

of different lengths [1]

18.  *Explain why methanol, ethanol, and propanol are generally soluble in water but larger alcohol molecules are not. [2]

19.  *What is the order of the boiling points of ethanal, ethane, ethanoic acid, and ethanol from lowest to highest? Explain how your derived your order. [4]

Part B – Application [35 marks]

1.  Provide the IUPAC name for each of the following molecules. [4]

a) b)

c) d)

2.  Provide 2 accepted names for each of the following molecules. [8]

a) b)

IUPAC #1: IUPAC #1:

Common: Common:

c) d)

IUPAC: IUPAC:

IUPAC #2: IUPAC #2:

3.  *Draw the structure of each of the following molecules in either expanded or condensed form. [10]

a) 3-bromo-1-propanol f) pentyl methanoate

b) cis-3,4-difluoroheptene g) 3,4-diethyl-2-hexanone

c) p-chlorohydroxybenzene h) 4-iodopentanoic acid

d) tetramethylbutane i) N-propyl butanamide

e) 3-s-butyl heptanal j) 4-ethyl-3-methyl-1-hexyne

4.  *Use balanced structural equations to illustrate the reactants and products needed for each reaction. You do not need to show the conditions of each reaction. [13]

a) the complete hydrogenation of 2-butyne [2]

b) the major and minor products of the hydrofluorination of 1-hexene [2]

c) the creation of 2-aminopentane from 2-iodopentane [2]

d) the synthesis of an ether from ethanol and 1-propanol [2]

e) the complete oxidation of 2-hexanol [1]

f) the synthesis of heptyl ethanoate [3]

g) the polymerization of CH2=CHBr [1]