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 form combinations 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:

1.  complete structural diagram – shows ______

eg) C3H8

C3H7F

2.  condensed structural diagrams – shows ______

______but includes the ______etc. attached to each carbon

eg) C3H8

C3H7F

3.  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 = di 7 = hepta

3 = tri 8 = octa

4 = tetra 9 = nona

5 = penta 10 = 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 branches get 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, then the ______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, then the ______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 corresponding aliphatics because of ______

eg) methane (CH4) BP = ______

methanol (CH3OH) BP = ______

·  ______

·  the ______end of the alcohol is ______while the ______end ______\ small alcohols are ______in water and large alcohols are ______

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 to lack of hydrogen bonding

·  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 ______