Chemistry 30 – Organic Review

1. Which of the following chemical compounds is not considered an organic compound?

A C2H5COOCH3(l)B C6H5COOH(s)C CH3CH2OH(l)D NH4CN(s)

2. Which of the following rows identifies the condensed structural formula or line diagram and IUPAC name of an isomer of C6H12?

3. Write the correct IUPAC name for each of the following:

a)

______________________________

b)

______________________________

c)

______________________________

d)

______________________________

CH2

CH3

CH2 = C – CH3

CH3

CH3

CH3 – CH – CH2 – CH2 – C – CH3

CH2

CH3

CH3 CH3

CH3

CH3 – CH – CH – CH

CH2 – CH2 – CH3 CH3

e)

______________________________

f)

__________________________________

g)

__________________________________

h)

__________________________________

i)

__________________________________

CH2 – CH3

CH3 CH3

CH3 – O – C – CH3

O=

F F

CH3 – CH – CH – CH3

O=

CH3 – CH2 – C – OH

CH3

OH

CH3 – CH2 – CH2 – C – CH3

Use the following structural diagrams to answer the next question

4. Match the general structural diagrams numbered above with the class of the compound below.

Carboxylic acid ________________ (Record in first column)

Aromatic ________________ (Record in second column)

Alcohol ________________ (Record in third column)

Ester ________________ (Record in fourth column)

(2 marks)

Use the following information to answer the next question

5. The structural diagram above represents an i compound that contains a _ ii _ and an iii functional group.

The statement is completed by the information in row

Row i ii iiiA aromatic carboxyl alkeneB aromatic hydroxyl esterC aliphatic carboxyl alkeneD aliphatic hydroxyl ester

(2 marks)

6. An organic compound reacted with brown Br2(aq) and the brown colour of the bromine remained unchanged in the aqueous layer. Which of the following would not be a possible identity for the compound?

A methylbenzeneB 2,2,4-trimethylpentaneC cyclopropaneD 2-methylbut-1-ene

Use the following diagram to answer the next question

7. The method of separating the mixture of hydrocarbon compounds in crude oil that is represented in the diagram above is (2 marks)

A titrationB precipitationC solvent extractionD fractional distillation

8. The type of reaction that occurs when ethene gas and chlorine gas react is _ i , and the name of the organic compound produced is _ ii .

The statement above is completed by the information in row:

Row i iiA addition 1,2-dichloroethaneB addition 1-chloroetheneC substitution 1,2-dichloroethaneD substitution 1-chloroethene

(2 marks)

Use the following information to answer the next question

Common Organic Reactions

1 C2H4(g) + H2(g) C2H6(g)

2 C2H5OH(l) C2H4(g) + H2O(l)

3 C6H6(l) + Br2(l) C6H5Br(l) + HBr(g)

4 CH3COOH(l) + CH3OH(l) CH3COOCH3(l) + H2O(l)

9. Match each equation representing the reactions numbered above with the type of reaction it exemplifies below: (2 marks)

Addition ________________ (Record in first column)

Substitution ________________ (Record in second column)

Elimination ________________ (Record in third column)

Esterification ________________ (Record in fourth column)

Use the following structural diagram to answer the next question

10. Which of the following monomers is required to produce the polymer in the structural diagram above?

Use the following information to answer the next question

There are several methods of producing chloroethane, which can be used as a solvent and a refrigerant.

11. Match the reactants and type of reaction numbered above with the two methods of producing chloroethane below. (2 marks)

Method I

___________ + Cl-Cl H – C – C – Cl + HCl which is a(n) ___________ reaction. Reactant Product(Record in (Record in 1st column) 2nd column)

Method II

___________ + H – Cl H – C – C – Cl which is a(n) ___________ reaction. Reactant Product(Record in (Record in 3rd column) 4th column)

H H

H H

H H

H H

Reactants Type of Reaction1 ethane 5 addition2 ethene 6 condensation3 ethyne 7 elimination4 ethanol 8 substitution

Use the following information to answer the next question

12. Match the IUPAC name or the organic term numbered above with its descriptor below:(2 marks)

Product name ________________ (Record in first column)

Reactant name ________________ (Record in second column)

Type of organic reaction ________________ (Record in third column)

Classification of product ________________ (Record in fourth column)

13. Using principles from throughout this course, explain why all hydrocarbon aliphatics and aromatics are insoluble in water.

14. Explain why cycloalkynes with fewer than eight carbons in the ring do not exist.

Use the following information to answer the next question

Compound Boiling Point(°C)

Solubility in waterat 25°C

I cyclobutane 12 very lowII propan-1-ol 98 high

III pentan-1-ol 138 high

15. a) Draw structural formulas for compounds II and III. (2 marks)

propan-1-ol pentan-1-ol

b) Explain why the boiling point of compound III is higher than the boiling point of compound II, and explain why compound II is more soluble than compound I.

(4 marks)