Chemistry 30

Organic Chemistry Notes

A. Carbon Compounds

30-C1.1k  define organic compounds as compounds containing carbon, recognizing inorganic exceptions such as carbonates, cyanides, carbides and oxides of carbon

  • organic compounds are those in which ______ atoms are almost always bonded to each other, to ______atoms and a few other atoms (______)
  • inorganic exceptions are the ______

______(no C-C bonds or C-H bonds)

eg) ______

  • there are ______ of organic compounds and all contain ______
  • carbon is unique for two reasons:

a)it can bond with ______atoms to form ______

b)it can formcombinations of ______

______(no other element does this!!!!)

  • recall polarity and intermolecular forces from the chemical bonding unit
  • polar bonds are formed when there is an ______ pull on e
  • ______ compounds are formed when the polar bonds within a molecule ______ each other out
  • the presence of ______forces and ______ will allow polar compounds to ______, since it is also polar
  • ______ compounds only have LD forces between molecules and ______dissolve in water

30-C1.2s  perform an experiment to compare the properties of organic compounds with inorganic compounds, considering properties such as solubility, viscosity, density, conductivity and reactivity

B. Structural Isomers

30-C1.5k  define structural isomerism as compounds having the same empirical formulas, but with different structural formulas, and relate the structures to variations in the properties of the isomers

  • isomers are compounds with the ______but a ______
Example 1

Draw the three structural isomers for C5H12.

1.2.3.

Example 2

Draw three structural isomers for C4H8F2.

1.2.3.

30-C1.3s  compile and organize data to compare the properties of structural isomers

  • different structures result in different ______
  • the arrangement of the atoms determines the types of intermolecular attractions which then determines properties such as ______and ______ in water

Example

Draw two isomers of C3H8O. Which one would have a boiling point of 7.4C and which would have a boiling point of 82.5C? Explain why the boiling points are so different.

C. Formulas and Structural Diagrams

  • organic molecules can be drawn in three different ways:
  • complete structural diagram – shows ______

eg) C3H8

C3H7F

  1. condensed structural diagrams – shows ______

______but includes the ______etc. attached to each carbon

eg) C3H8

C3H7F

  1. line structural diagrams – shows only ______

______bonds

eg)C3H8

C5H12

C4H8

30-C1.2s  build molecular models depicting the structures of selected organic and inorganic compounds

Your Assignment: pg 1

D. Prefixes

1. Number of Functional Groups

6 = hexa

2 = di7 = hepta

3 = tri8 = octa

4 = tetra9 = nona

5 = penta10 = deca

2. Number of Carbons

1 = ______6 = ______

2 = ______7 = ______

3 = ______8 = ______

4 = ______9 = ______

5 = ______10 = ______

30-C1.2k  identify and describe significant organic compounds in daily life, demonstrating generalized knowledge of their origins and applications

30-C1.3k  name and draw structural, condensed structural and line diagrams and formulas, using IUPAC nomenclature guidelines, for saturated and unsaturated aliphatic (including cyclic) and aromatic carbon compounds

30-C1.1sts  explain how science and technology are developed to meet societal needs and expand human capability

30-C1.2sts  explain that science and technology have influenced, and been influenced by, historical development and societal needs

30-C1.3s  follow appropriated IUPAC guidelines when writing the names and formulas of organic compounds

E. Alkanes

eg) ______

  • hydrocarbons containing ______between the carbons ie) they are ______
  • can be ______continuous chains, ______chains, ______structures ______

1. Properties

  • ______ in water
  • can be ______ depending on number of carbon atoms
  • relatively ______because the ______bonds are ______

2. Uses

  • natural gas, BBQ’s, lighter fluid, gasoline etc
  • good for making plastics, lubricants

3. Naming

  • IUPAC = International Union of Pure and Applied Chemistry

i. Continuous Chains

  • ______

eg)

ii. Branched Chains

  • branches are called ______functional group
  • 1 C = ______; 2C = ______; 3 C = ______ etc
  • find the ______and ______so the branches get the ______

possible numbers

  • to name: name the ______first(in ______order),including the ______where each group is found, then name the ______

______(parent name)

eg)

Try These:

1.

2.

3.

4.

Try These

Draw the structure for each of the following compounds:

1. 2,2-dimethylpropane

2. 4-ethyl-2,3-dimethylhexane

3. 4-propyloctane

4. 3,5-diethyl-4-methylheptane

Your Assignment: pgs 2-3 in workbook

iii. Cycloalkanes

  • use the ______as the ______ name
  • ______+ ______+ ______

eg)

  • if there are branches, number the carbons in the ring so the branchesget the ______

eg)

Try These:

1.

2.

3.

4. 1,2-dimethylcyclopropane

5. 1,1,2,2-tetraethylcyclohexane

6. 3-butyl-1,1,2-trimethylcyclopentane

Your Assignment: pg 4 in workbook

C. Alkenes

eg) ______

  • hydrocarbons containing ______ie) they are ______
  • can be ______continuous chains, ______chains, ______structures ______

1. Properties

30-C1.3s  interpret the results of a test to distinguish between a saturated and an unsaturated aliphatic, using aqueous bromine or potassium permanganate solutions

  • ______ in water
  • ______ than corresponding alkane because they have ______which makes the ______forces of attraction ______

eg) ethane BP = 88.6C ethene BP = 103.8C

  • ______than alkanes
  • double bond has ______in the same area

______and ______

______

  • diagnostic test: use ______***alkenes ______with these substances causing a noticeable ______, alkanes will not

2. Uses

  • plastics (PVC)
  • steroids
  • welding torches

3. Naming

i. Continuous Chains

  • ______
  • number carbons to give the ______the ______
  • the number where the double bond ______is to be given as a “ # ” between the prefix and the suffix

eg)

ii. Branched Chains

  • find the longest carbon chain and number it so the ______gets the ______ number
  • to name: name the ______first(in ______order), including the ______of the carbon where each is found, thenthe ______including the ______ of the carbon where the double bond starts

eg)

Your Assignment: pgs 5-6 in workbook

iii. Cycloalkenes

  • double bond is always numbered ______
  • ______get the ______ numbering sequence after the ______
  • ______+ ______+ ______
  • list branches in ______with the ______ of the carbon they are on

eg)

Your Assignment: pg 7 in workbook

D. Alkynes

eg) ______

  • hydrocarbons containing ______ie)they are also ______
  • can be ______continuous chains, ______chains
  • not plentiful in nature

1. Properties

  • ______
  • ______(more than alkanes and alkenes)
  • ______bond has ______in the same area ______ force of repulsion
  • boiling points are ______ than corresponding alkanes and alkenes because of their ______and the ______ of triple bonds

2. Uses

  • welding torches

3. Naming

i. Continuous Chains

  • ______
  • number carbons to give the ______the ______
  • the number where the triple bond ______is to be given as a “ # ” between the prefix and the suffix

eg)

ii. Branched Chains

  • find the ______and number it so the ______ gets the lowest number
  • to name: name the ______first(in ______order), including the ______of the carbon where each is found, thenthe ______including the ______ of the carbon where the triple bond starts

eg)

Your Assignment: pg 8 in workbook

Review
  • alkanes – branches, rings – least reactive
  • alkenes – branches, rings
  • alkynes – branches – most reactive
  • all called ______
  • all ______and ______in water
  • major intermolecular forces are ______boiling points are ______

E. Aromatics

  • hydrocarbons containing one or more ______
  • all bonds are the ______we draw benzene like this:

1. Properties

  • ______
  • the benzene ring structure is ______
  • aromatics are characterized by strong aromas

2. Uses

  • ASA, amphetamines, adrenaline, benzocaine (anesthetic)
  • moth balls, TNT
  • wintergreen, menthol, vanilla, cinnamon
  • SPF in sunscreen

3. Naming

i. Benzene as a Branch

  • if you have a really long carbon chain, it is easier to call the benzene ring a ______

eg)

ii. Benzene as the Main Compound

  • if only one group is attached, give the ______attached to ______

eg)

  • if there is more than one branch, number them so they get the ______and name ______

eg)

***watch out for this!

Your Assignment: pgs 9-10 in workbook

30-C1.4k  identify types of compounds from the hydroxyl, carboxyl, ester linkage and halogen functional groups, given the structural formula

F. Alcohols

  • organic compounds with one or more ______

______

1. Properties

  • have much ______than correspondingaliphatics because of ______

eg) methane (CH4) BP = ______

methanol (CH3OH) BP = ______

  • ______
  • the ______end of the alcohol is ______while the ______end ______small alcohols are ______in water andlarge alcoholsare ______

2. Uses

  • antifreeze, rubbing alcohol, beverages, moistening agent

3. Naming

  • number the longest carbon chain containing the ______so the ______group gets the ______
  • ______name (______at end) + ______
  • give the ______where the ______ is found between the parent name and the suffix
  • if there is ______ hydroxyl group, use a prefix (______) to indicate the ______ of OH groups and place the numbers between the parent name and the suffix

***Note, if the suffix starts with a vowel, drop the “e” on the parent name; if the suffix starts with a consonant, keep the “e” on the parent name

eg)

  • an unusual case:

Your Assignment: pg 11 in workbook

G. Organic Halides

  • where ______is ______and ______is a ______
  • organic compounds where ______has been replaced by ______
  • do not readily occur in nature

1. Properties

  • can be ______or ______, depending on the placement of the halogen groups
  • many are ______

2. Uses

  • manufactured for human use eg) DDT, PCB, CFC
  • anesthetics
  • dry cleaning fluid
  • plastics, polymers (Teflon)

3. Naming

  • same rules as before…name branches (______included now) ______

F = ______Cl = ______

Br = ______I = ______

eg)


Your Assignment: pg 12 in workbook

H. Carboxylic Acids

  • where ______is ______
  • organic compounds containing the ______

______

  • considered ______ since double bonds in functional groups are not taken into account

1. Properties

  • ______
  • ______boiling points due to ______
  • ______
  • diagnostic test: use ______(will turn ______), readily react with ______, ______

2. Uses

  • recycling rubber – methanoic acid
  • vinegar – ethanoic (acetic) acid
  • rust remover – oxalic acid
  • fruits – citric acid

3. Naming

  • count the longest carbon chain including the ______in the ______
  • the carbon in the carboxyl group is always number ______
  • drop ______and add ______

eg)

Your Assignment: pg 13 in workbook

I. Esters

  • where ______ can be a carbon chain or hydrogen and ______ can be a carbon chain
  • combination of a ______and an ______
  • considered ______ since double bonds in functional groups are not taken into account

1. Properties

  • ______
  • ______esters ______in water, ______esters ______
  • boiling points slightly lower than corresponding carboxylic acids and alcohols due tolack ofhydrogenbonding
  • very ______which allows them to generate ______

2. Uses

  • flavouring agents

3. Naming

  • identify the ______ used to make the ester
  • change the alcohol name to the corresponding ______ name

eg) methanol would become ______

  • identify the ______ the ester was made from
  • drop the “oic acid” and replace with ______

eg) butanoic acid would become ______

  • put the ______together with a ______ in between

eg) ______

  • you can have ______ on esters…they follow the alphabetical rule, numbering begins at the ______ of the alcohol and the C=O end of the carboxylic acid

eg)

Your Assignment: pg 14 in workbook

J. Boiling Points and Solubility

30-C1.6k  compare, both within a homologous series and among compounds with different functional groups, the boiling points and solubility of examples of aliphatics, aromatics, alcohols and carboxylic acids

  • we can compare the boiling points of various organic compounds using their ______and the ______

______between the molecules

Example 1

Put the following organic compounds in order from highest boiling point to lowest boiling point.

alcohol, alkane, alkene, aromatic, carboxylic acid

Example 2

Put the following homologous series of organic compounds in order from highest boiling point to lowest boiling point.

C2H6, C2H5OH, CH3COOH, C2H4

  • we can also compare the ______of various organic compounds using their polarity

Insoluble Organic Compounds / Soluble Organic Compounds

K. Organic Reactions

30-C2.1k  define, illustrate and provide examples of simple addition, substitution, elimination, esterification and combustion reactions

30-C2.2k  predict products and write and interpret balanced equations for the above reactions

30-C2.4k  relate the reactions described above to major reactions that produce thermal energy and economically important compounds from fossil fuels

30-C2.3s  use IUPAC conventions when writing organic chemical reactions

1. Combustion Reactions

  • occurs when a ______reacts with ______
  • products are always ______

______

  • these are economically important reactions for they are the major reactions that produce ______required for fuelling our vehicles, heating our homes, and producing electricity

eg)___ C5H12(l) + ___ O2(g) 

+ ____ O2(g) 

2. Addition Reactions

  • a ______or ______ bond in an alkene or alkyne is ______ and a group or element is ______

eg)

Try These:

1.

2.

3.

Your Assignment: pg 15

3. Substitution Reactions

  • the replacement (______) of a hydrogen on an alkane or aromatic with ______ (eg. F, Cl etc)
  • commonly used to make ______

Examples:

4. Esterification Reactions

  • the reaction of a ______with an ______
  • the catalyst is ______

Examples:

5. Elimination Reactions

  • an ______ has water removed, forming and ______plus the ______
  • ______can react with a ______to produce an ______, a ______and ______

Examples:

3.

Your Assignment: pgs 16-17

6. Polymerization Reactions

30-C1.2sts  explain that science and technology have influenced, and been influenced by, historical development and societal needs

30-C2.3k  define, illustrate and provide examples of monomers, polymers and polymerization in living systems and nonliving systems

30-C2.3s  draw or use models to illustrate polymers

  • a ______is a ______that forms the ______ for a polymer
  • a ______is a ______formed by the ______of ______
  • depending on the polymer, the monomers that make it up can be ______or ______
  • polymers can be ______

eg) ______

  • polymers can be ______

eg) ______

  • polymers that can be heated and molded into specific shapes are commonly called ______
  • plastics are one type of synthetic compound that has been of great benefit to society (although there are also problems associated with then)
  • the names of polymers are the monomer name with ______ in front
  • many have classical names instead of IUPAC names

Addition Polymers

  • formed when the electrons in double or triple bonds in the monomer units are rearranged
  • the polymer is the ______ formed

Examples:

Condensation Polymers

  • polymerization reactions that involve the formation of a ______

______ (commonly ______) as well as the ______

  • each monomer must have ______ functional groups
  • two common linkages formed:
  1. ______ linkage – between carboxyl group (COOH) and hydroxyl group (OH)
  2. ______ linkage – between amino group (NH2) and carboxyl group (COOH)

Examples:

K. Petroleum Refining

30-C1.7k  describe, in general terms, the physical, chemical and technological processes used to separate organic compounds from natural mixtures or solutions

30-C2.1sts  explain how science and technology are developed to meet societal needs and expand human capability

  • Alberta has vast reserves of petroleum in the form of natural gas, crude oil and oil sand deposits
  • most of this petroleum is refined and then burned as ______
  • petrochemicals, basic hydrocarbon raw materials such as ethane and propene, are also used in the production of ______
  • refining of petroleum separates the crude mixture into purified components
  • ______ is used to separate the components
  • distillation works because of the different ______ of the components of petroleum
  • the ______the molecule and the ______the boiling point, the ______ it rises in the tower (asphalt, fuel oil, wax at bottom; gasoline at top)
  • there are two types of reactions in petroleum refining:

1. Cracking

  • ______longchain hydrocarbons into ______
  • cracking requires heat and pressure
  • there are many different types of cracking reactions, forming different products (alkanes, alkenes)

eg) catalytic cracking, steam cracking, hydrocracking

  • hydrocracking requires ______

Examples:

1. C9H20 + C8H18

2. Reforming

  • small hydrocarbons are ______to make ______
  • requires heat and pressure
  • there are several types of reforming reactions

eg) alkylation to produce “high octane” gasoline

  • all reforming reactions produce ______

Examples:

1. C7H16 + C12H26

2. ethane + octane

30-C1.1s  design a procedure to separate a mixture of organic compounds, based on boiling point differences

Your Assignment: pgs 18-19

Separate an Organic Mixture – pg 581

Organic Reactions and the Environment Assignment

Chemistry 30 Organic Chemistry1Jill Agnew