Organic Chemistry Notes

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

condensed structural diagrams – shows ______

______but includes the ______etc. attached to each carbon

eg) C3H8

C3H7F

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:

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:

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:

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:

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:

______ linkage – between carboxyl group (COOH) and hydroxyl group (OH)
______ 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