Chemistry 30: Organic Chemistry Workbook

1. Differentiate between an organic and inorganic compound. Provide an example of each. - organic compounds are those in which carbon atoms are almost always

bonded to each other, to hydrogen atoms and a few other atoms (O, N, S, P)

2. List the classes of inorganic compounds that contain carbon. inorganic exceptions are the oxides of carbon, carbonates, cyanides and carbides

a. eg) CO2, CaCO3, NaCN, SiC

3. Identify the following compounds as organic or inorganic. Justify your choice.

a. Carbon monoxide inorganicb. CH3CN organicc. CoCO3 inorganicd. Carbon inorganice. CaO inorganicf. C6H6 organicg. Water inorganich. NaCN inorganici. CCl4 organicj. CO2 inorganic

1. With the help of an example, explain the difference between structural, condensed structural, and line diagrams.

a. Complete structural shows ALL bonds

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C1: I can define organic compounds and recognize the exceptions and I can identify and describe significant organic compounds in daily life.

C2: I can name and draw and build structural, condensed structural, line diagrams, and molecular formulas for saturated and unsaturated aliphatic (including cyclic) and aromatic compounds. Including: alcohols, carboxylic acids, esters, halogenated hydrocarbons

I can identify types of compounds from their functional groups.

b. Condensed structural shows C-C bonds, include s hydrogens/others attached to carbon

c. Line diagrams shows only C-C bonds, no hydrogen, shows other elements

2. What is meant by the term homologous series?group of organic chemical compounds, usually listed in order of increasing size,that have a similar structure (and hence also similar properties) and whose structures differ only by the number of CH2 units in the main carbon chain.

3. Write the molecular formula and draw the condensed structural and line diagrams for the following:

a. Propane

b. 2-2-dimethylpentane

c. Cyclobutane

d. Ethylcyclopropane

4. Name the following organic compounds and draw the condensed structural formula:

a.

2-methylbutane

b. 3-methylheptane

c. 1-ethyl-2-methylcyclopropane

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d. 4-ethyl-6-methylheptane

5. How does a cycloalkane differ from an alkane? Explain using general formulas.

Closed ring of C-C bonds, General formula is CnH2n

6. Write the molecular formula and draw the condensed structural and line diagrams for the following:

a. hept-3-ene C7H14

b. 2-methylhex-3-ene C7H14

c. 5,5-dimethylhex-2-yne C8H14

d. 1,2-dipropylcyclobutene C10H18

7. Name the following organic compounds and draw the condensed structural diagram:

a. 4, 4-dimethylpent-2-ene

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b. 3-ethyl-2-methylcyclobutene

c. Hex-2-yne

8. Explain how one can differentiate between an alkane, alkene, and alkyne by the name and by a diagram.

Look for multiple bonds in the diagram, look at the suffix within the name

9. Using general formulas explain which of the following family groups are isomers of one another. State if the each family is saturated or unsaturated.

a. Alkanes CnH2n+2

b. Alkenes CnH2n

c. Alkynes CnH2n-2

d. Cycloalkanes CnH2n

e. Cycloalkenes CnH2n-4

10.Identify all the families that the following molecular formulas belong to:

a. C2H4 alkene or cycloalkane

b. C3H8 alkane

c. C4H6 alkyne

d. C5H10 alkene or cycloalkane

11.Differentiate between an aliphatic and aromatic hydrocarbon. Provide an example of each and write the molecular formula for your examples.

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Alkenes and cycloalkanes are structural isomers of each other

Aliphatics includes straight, branched or rings of alkanes, alkenes and alkynes

Aromatics are organic compounds with a structure based on benzene or benzene-like rings

12.Draw the line diagrams and list the molecular formulas for the following organic compounds:

a. ethyl benzene

b. 3-phenyloctane

c. 1-ethyl- 2-methylbenzene

13.Name the following organic compounds:a.

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1,2,4 - trimethylbenzene

b.1, 4 - diethylbenzene

c.

pentylbenzene

d.

2-methyl-5-phenylheptane

14.Explain and illustrate the difference between cyclohexane, cyclohexene and benzene. Explain the difference in chemical reactivity of these three compounds.

Increase of # of muliple bonds of the closed ring carbons.

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Benzene most stable: react like straight alkanes, resonance structure of benzene

Cyclohexane : increased bond angle strain

cyclohexene least stable: increased bond angle and multiple bond strain

15.Draw the line diagrams for the following organic halide/halogenated hydrocarbon compounds:

a. Tetrachloromethane

b. bromoethane

c. 2-bromopropane

d. 2-bromo-2-methylpropane

e. 3-iodo- 2,2-dimethyloct-4-ene

f. bromocyclopropane

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16.Name the following organic compounds and circle the functional group:

a.

bromobenzene

b.

2, 2 - dibromobutane

c.

1-bromo-4-fluorobutane

17.Provide the complete structural diagram and name the following compounds:

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a. CHF2Cl chlorodifluoromethane

b. CH3CFCl2

1,1-dichloro-1-fluoroethane

c. CCl2F2

dichlorodifluoromethane

18.What is the general formula and the name of the functional group of an alcohol?

R - OH , functional group called a hydroxyl (OH) group

19.Draw the line diagrams for the following organic compounds:

a. butanol

b. 3-methylbutan-2-ol

c. hexane-1,2-diol

d. 2-bromo- 3-methylheptanol

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20.Name the following alcohol compounds:a.

b.

c.

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21.Write the molecular formula and draw the structural formulas and line diagrams for the following organic compounds:

a. octanoic acid

b. benzoic acid

c. propanoic acid

22.Name the following organic compounds:a.

b. HOOC-CH2-CH2-CH2-CH3

c.

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23.Draw the structural formulas and line diagrams for the following organic compounds:

a. propylbutanoate

b. butylpentanoate

c. methyl ethanotae (structural diagram only)

24.Name the following organic compounds:a.

b.

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c.

d.

25.Identify two sets of isomers using the chemical compounds in questions 21-24.

26.Complete the following table and provide an example of each compound.

Compound Name and Draw the functional group

General Formula Example

Alkane Single bond R-R CnH2n+2 ethane

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Alkene

Alkyne

Benzene

Organic Halide/ Halogenated Hydrocarbon/ Alkyl Halide

Alcohol

Carboxylic Acid

Ester

1. Define the term “structural isomer”.

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C3: I can define and recognize structural isomers

2. Provide ALL non-cyclic structural isomers of C5H10. (There are 5)

3. Provide three structural isomers of C4H6.

4. Which one of the following compounds is an isomer of CH3CH2CH2CH2OH? Justify your answer.

(a) CH3CH2CH2OH (b) CH3CH(OH)CH3 (c) CH3CH2CH2CHO (d) CH3CH2CH2CH3 (e) none of the above

5. Draw and name three isomers of C3H6Cl2.

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6. Provide and name three isomers of a five carbon alcohol.

1. Using the following table, explain the differences in boiling points. Write the molecular formula of these isomers.

2. Explain why alkanes are immiscible in water

3. Describe a solvent that they would be miscible in.

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C4: I can compare boiling points and solubility of organic compounds I can describe the process involves in separating organic compounds from natural mixtures I can design a procedure to separate a mixture of organic compounds based on boiling point

differences

4. Why does methane have a lower boiling point than ethane?

5. Are alkenes and alkynes miscible in the following solutions. Explain your answer.

a. water

b. benzene

c. tetrachloromethane

6. Explain a physical method that is used to separate crude oil into fractions. What property is used for this separation?

7. Explain how bitumen is extracted from oil sands. What property is used for this extraction.

8. Using the fractionation distillation tower below, explain why Gas is collected at the top and Fuel Oil is collected near the bottom.

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9. Explain why alcohols are miscible with water.

10.Explain which is more miscible in water, methanol or butanol.

11.Explain why carboxylic acids are more polar than alcohols and esters.

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12.Explain which is more soluble hexanoic acid or 2,3, - dimethylbutanoic acid.

1. Differentiate between a saturated and unsaturated hydrocarbon.

2. Explain what one would expect to see when bromine is added to propene and added to propane.

3. Describe a test you would use to differentiate between cyclohexane, cyclohexene and benzene.

4. Are esters and carboxylic acids saturated or unsaturated? Explain.

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C5: I can determine the saturation and interpret tests that check for the saturation of a hydrocarbon.

C6: I can define, illustrate, provide examples, and predict products for of addition, substitution, elimination, esterification, and combustion reactions.

1. Explain the difference between an addition and substitution reaction.

2. Identify possible product(s)/ reactant(s) and the type of reaction that occurred for the following: Draw the structures to help you visualize the reactions.

a. propane + chlorine

b. ______ + _______ ethanol

c. 2-chlorohexane + hydrogen iodide

d. benzene + iodine

e. ethyne + excess hydrogen

f. prop-2-ene + bromine

3. What reaction type produces an alcohol and what reactants are needed?

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4. What is the relationship between an elimination reaction and an addition reaction?

5. Illustrate the following reactions and identify the type of reaction that is taking place:

a. The formation of hexan-2-ol from an alkene.

b. The reaction between 2-bromobutane and iodine gas.

c. A reaction that forms potassium bromide, water and but-2-ene.

d. The reaction between water and cyclohexene.

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e. The reaction between benzene and iodine gas.

f. A reaction that forms prop-2-ene and water.

6. What two reactants are necessary in order for an esterification reaction to occur, and what conditions are necessary?

7. What inorganic by-product is always formed in an esterification reaction?

8. Predict the name of the organic compound formed , its by-product, or reactants for the following reactions:

a. methanol + butanoic acid

b. _______________ + methanoic acid ethylmethanoate +

c. pentanol + __________________ pentylethanoate +

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9. Name the following esters, and the acids and alcohols from which they were prepared:

a. CH3CH2COOCH2CH3

b. CH3CH2CH2COOCH3

c. HCOOCH2CH2CH2CH3

d. CH3COOCH2CH2CH3

10.Explain the difference between a complete and incomplete combustion reaction.

11.Write the balanced chemical equations for the following reactions:a. The complete combustion of 3-methylhexane

b. The incomplete combustion of benzene

c. The complete combustion of cyclohexane

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d. The incomplete combustion of octane.

12.Explain how to recognize the following reactions:a. Addition

b. Substitution

c. Elimination

d. Esterification

e. Complete combustion

f. Incomplete combustion

1. Draw the polymers that are created from the following monomer subunits:a. but-1-ene

b. 1-chloro-1,2,2-trifluroethene

c. propyne

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C7: I can define, illustrate and provide examples of monomers, polymers, and polymerization

2. Draw and name the monomer that formed the following polymersa.

b.

c.

3. What functional group(s) must be present in a monomer that undergoes an addition polymerization reaction?

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4. Explain the differences between addition polymerization reactions and condensation polymerization reactions?

5. Explain why the below is a condensation polymerization reaction. List the families that the polymer belongs to.

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