10.1 - Introduction - questions

1 - What is an organic compound ?

2 - Describe the features of a homologous series !

3 - Predict and explain the trends in boiling points of members of a homologous series !

4 - Describe the difference between empirical, molecular and structural chemical formulas !

5 - What are structural isomers ?

6 - What is the first rule of the IUPAC system ?

7 - What is the second rule of the IUPAC system ?

8 - What is the third rule of the IUPAC system ?

9 - Give the name of the ending if a formula contains the following:

10 - Give the name of the ending for the following cases:

11 - Give the names for the following formulas:

12 - Give the names for the following formulas:

13 - Give the names for the following formulas:

14 - Classify the alcohols above in primary, secondary and tertiary molecules !

15 - Give the formulas for the following compounds:

16 - Give the formulas for the following compounds:

17 - Give the formulas for the following compounds:

18 - Give the formulas and names for the following compounds:

19 - What two things have to be considered when predicting physical properties ?

20 - What is volatility ?

21 - What are the rules for predicting volatility ?

22 - What are the rules for predicting solubility in water ?

10.2 - Alkanes - questions

23 - Alkanes are saturated hydrocarbons, what does that mean ?

24 - Does alkanes have low or high reactivity ? Explain why !

25 - Use C3H8 as an example to explain with formulas complete and incomplete combustion of alkanes !

26 - What is a free radical and what is the difference to an ion ?

27 - What is homolytic fission ?

28 - What is the main reaction that alkanes undergo ?

29 - Explain the stages of the reaction between chlorine and methane to form chloromethane !

10.3 - Alkenes - questions

30 - Alkanes are unsaturated hydrocarbons, what does that mean ?

31 - What is the main reaction that alkenes undergo ?

32 - Give 4 examples of reactions with ethene.

33 - What tests can be made to see if one has an alkane or alkene ?

34 - What is polymerization of alkenes ?

35 - Give examples of how plastics are created from polymerization of alkenes.

10.4 - Alcohols - questions

36 - What are the general formulas for alcohols, alkenes, alkanes and halogenoalkanes ?

37 - How does the physical properties of alcohols compare with alkanes ?

38 - Describe, using equations, the complete combustion of alcohols.

39 - Describe, using equations, the oxidation of alcohols.

10.5 - Halogenoalkanes - questions

40 - What is a nucleophile ?

41 - What is heterolytic fission ?

42 - Describe the reactions with halogenoalkanes !

43 - What does it mean that a reaction is unimolecular and bimolecular ?



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10.1 - Introduction

An organic compound contains carbon and in almost all cases also hydrogen.


A homologous series is a family of organic compounds.

Features:
1. Successive members of a homologous series differ by a -CH2 group.
2. Members of a homologous series can be represented by the same general formula (for example CnH2n+2)
3. Members of a homologous series show a gradiation in physical properties (such as boiling point, density and viscosity).
4. Members of a homologous series have similar chemical properties (such as chemical reactivity).


The length of the carbon chain determines the boiling point with compounds with more carbon atoms having higher boiling points. As the molecules get larger and larger, the van der Waals forces between them increases and this makes the boiling point go up.


Empirical formulas: Give the ratios of the atoms in the molecule (example Ethanoic acid: CH2O).

Molecular formulas: Give the actual numbers of atoms in the molecule (example Ethanoic acid: C2H4O2).
Full structural formula: Shows every bond and atom (example Ethanoic acid :  )
Condensed structural formula: Omits bonds when they can be and groups atoms together (example Ethanoic acid CH3COOH)
Stereochemical structural formula: Shows relative postion of atoms in three dimensions (example :  )


Molecules that have the same molecular formula but different arrangement of the atoms are called structural isomers and they have typically different chemical properties. Butane and 2-metyl propane for example have both the chemical formula C4H10 but the carbon and hydrogen atoms are bound together differently giving different properties (see figure on page 375).


The longest chain of carbon atoms in the molecule gives the stem of the name.

Rule to remember: ME EAT PROPER BUTTER called PENT-HEX

1 carbon atom in longest chain is meth-
2 carbon atom in longest chain is eth-
3 carbon atom in longest chain is prop-
4 carbon atom in longest chain is but-
5 carbon atom in longest chain is pent-
6 carbon atom in longest chain is hex-


Identify the functional group because that gives the ending (or suffix) to the name. If for example there is a -OH group in the molecule then it is an alcohol and the name ends with -anol.


Identify the side chains of substituent groups and see what the number is of the carbon atom in the main chain that it is attached to. The name of these side chains will give the first part of the name (the prefix).

-CH3 is called methyl-
-C2H5 is called ethyl-
-C3H7 is called propyl-
-NH2 is called amino-
-F is called fluoro-
-Cl is called chloro-
-Br is called bromo-
-I is called iodo-























The two things that have to be considered when predicting physical properties are:

1. The length of the CHn chain (the hydrocarbon skeleton).
2. The functional group.


Volatility is how easy a compound goes from liquid to gas.

High volatility = Low boiling point.

High volatility = weak intermolecular forces.


Hydrocarbon skeleton

1. Larger molecules have stronger van der Waals forces between them = Higher boiling point

2. Straight chained molecules without branches have stronger van der Waals forces between them = Higher boiling point

Functional group

3. Functional groups that are polar will develop dipole-dipole interaction = Higher boiling point



Note: Halogenoalkanes are alkanes with side chains containing Cl-,Br-, F- or I- atoms.


The solubility is determined by the extent to which molecules can form hydrogen bonds with water.

Hydrocarbon skeleton

1. Smaller molecules = Higher solubility

Functional group

2. Functional groups that enables hydrogen bonds = Higher solubility



10.2 - Alkanes

Hydrocarbon = compound that contains only hydrogen and carbon.

Saturated = compound with only single carbon-carbon bonds.


Alkanes have a low chemical reactivity because:

1. The C-C and C-H bonds are strong and therefore a strong source of energy is needed to break these bonds.

2. The C-C and C-H bonds are non-polar and therefore do not react with most reactants.





Free radical: contains unpaired electrons and is therefore very reactiv. Example: Cl* contains 7 electrons in the outer shell.

Ion: has lost or picked up electrons and is therefore charged. Example: Cl- contains 8 electrons in the outer shell because it has picked one up.


Homolytic fission: When a bond breaks by splitting the shared electrons so that two free radicals are produced (each with unpaired electrons).

Example Cl2:




Since alkanes are saturated hydrocarbons they undergo substitution reactions in which one of the hydrogen atoms in the alkane is swapped for another atom. An example is halogenation in which the news atom is a halogen such as Cl, BR, I or F.




10.3 - Alkenes

Hydrocarbon = compound that contains only hydrogen and carbon.

Unsaturated = compound with at least one double carbon-carbon bond.


Since alkanes are unsaturated hydrocarbons they undergo addition reactions in which the double bond is broken so that new bonding positions are created and the compound becomes saturated (only single bonds).





1.Alkenes undergoes addition reactions easily but not alkanes. If one put alkanes and alkenes in red bromide water it will become clear for alkenes because of reactions with the bromide but not with alkanes.

2. If one burn alkanes and alkenes, the alkenes have a dirtier, smokier flame because they have a higher ratio of carbon to hydrogen atoms. Compounds with benzene rings are very unsaturated (have many double bonds) and have even dirtier flames because of even higher carbon to hydrogen ratios.


The process of making long chains of thousands of atoms (polymers) from alkenes by breaking their double bonds are called polymerization. Plastics are typical polymers.

The alkene used is called the monomer and determines the chemical properties of the polymer.




10.4 - Alcohols

Alkanes: CnH2n+2

Alkenes: CnH2n

Alcohols: CnH2n+1OH

Halogenoalkanes: CnH2n+1X where X = halogen = F, Cl, BR, I


The -OH group is polar and increases therefore volatility and water solubility compared to alkanes.


Burning of methanol:

2CH3OH(l) + 3O2(g)   →   2CO2(g) + 4H2O(g)

Longer alcohol molecules will release more energy per mole due to the increasing number of CO2 molecules that are produced in the reaction.




10.5 - Halogenoalkanes

Nucleophile: An electron-rich species that is attracted to parts of other molecules that are electron deficient. They have a lone pair of electrons and might carry negative charge.

Examples: H2O, NH3,OH-, CN-


Heterolytic fission is when a bond breaks with both the shared electrons going to one of the products. It produces two oppositely charged ions.