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Unit 1 – Organic Chemistry

What is Organic Chemistry?

As early as _________, chemists recognized a difference between “organic” and “inorganic” compounds.

In 1828, Frederich Wöhler discovered that ________ - an organic compound - could be made by heating ammonium cyanate (an inorganic compound).

Organic Chemistry came to mean the chemistry of compounds from ____________ things but we now know that this definition is too limited.

Study of compounds that contain _____________ – organic compounds.

These are compounds where ______________ is bonded to another C or to H and sometimes to O, N, S or P.

Exceptions are CO32-, CN- ,C2

2-, oxides of C.

Inorganic Compounds

Anything that doesn’t contain carbon except for complex ions that contain carbon, carbide ion and oxides of carbon.

Nature of Carbon

Half filled outer shell (4 v.e)

Can bond to ____ other atoms

Intermediate electronegativity

More likely to _________ than gain/lose electrons.

Isomers

Same number of atoms, different ___________

Two types:

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Constitutional Isomers or Structural isomers – different SEQUENCE of atoms.

Stereoisomers – same atoms and sequence but different _____ orientation.

Diastereomers – double bonds. There are “cis” and “trans” isomers. The

C atom must have 2 different groups.

______________________ – C bonded to 4 different groups. Mirror

image – NOT superimposable.

Hydrocarbons

Contain only carbon and ________________________

Classified by type of carbon-carbon bond (single, double or triple).

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_______________________ hydrocarbons are those whose carbon backbone forms a straight chain, branched chain(s), or a ring (cyclic) structure.

When a hydrocarbon chain is attached to a main chain, it is called an ___________________.

_______________________ hydrocarbons are unique ringed structures based on benzene. The bonds have properties intermediate between single and double bonds.

Textbook Reading – pages 8-13

Textbook Questions – page 14: #1-7, 12.

Hydrocarbons

Alkanes

Single bonds

Saturated (with_____)

CnH2n+2

Non-polar, insoluble, small- ______________, med-liquids, large – waxy solids.

Methane, ethane, propane, butane

Naming Rules

See Page 17 for further explanation of naming rules.

1. Find the longest continuous chain of carbons in the molecule and name it. This is the parent chain of the molecule. Be careful, the longest continuous chain is not always obvious because it may zigzag. (HINT! highlight the parent chain in some way.)

2. Number the carbons in the parent chain. Designate the carbon at the end to which branching is closest as number 1.

3. List the alkyl groups present.

4. If there is more than one type of alkyl group in the molecule you can list their names in alphabetical order. 

5. If an alkyl group occurs more than once, use a Latin prefix to indicate the number present. The Latin prefixes are di = 2, tri = 3, tetra = 4, pent = 5, and so on. - e.g. two methyl groups would be represented as dimethyl

6. Use a number to indicate the location of each alkyl group on the parent chain. 

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7. Use proper punctuation: commas are used to separate numbers, and hyphens are used to separate numbers and letters. 

Alkyl Branches

1) Use prefix for branch based on number of carbons in chain + yl (methyl, ethyl, etc.)

2) Write the number of the location (point of attachment) of the branch using the lowest possible numbers.

3) Numerals separated by commas, numerals and letters separated by hyphens, branches and parent chains are not separated.

Naming Reference Table

Name and draw the following continuous-chain hydrocarbons:

1. C6H14    

2. C10H22    

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Another common way to represent a ____________________ is to use a condensed structural formula. For example, the chemical formula of C4H10 can be represented as: 

3. Write the name of the following:

4.

5. Draw the structural formula for the following:

2,3-diethyl-4,5-dimethylhexane

Online Practice: http:// www.docbrown.info/page06/DFalkanes/DFalkaneQmc.htm

Textbook Reading: Pages 15-21

Textbooks Questions: Page 19: #1-11

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Alkenes and Alkynes

Alkenes

Double _____________

Unsaturated (not the maximum # of H bonded)

CnH2n

Non-polar, _________________, location of double bond affects bp.

Naming

Similar to alkanes but number Carbon so that the carbons involved in double bond get lowest number.

The number of the first carbon involved in the double bond becomes a part of the suffix. i.e: “-2-ene”

Examples –Name them!:

Reading – Page 22-26

Practice – Page 26, #23-34

Extra Practice – page 27, #35-44

Alkynes

_______________ bond

unsaturated

CnH2n-2

Example: acetylene (fuel used in welding)

Non-polar, insoluble, higher bp than corresponding alkanes.

Naming

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Similar to alkenes except ______________ contains position of triple bond and “yne” i.e. “-3-yne”

Name it!

Reading – page 28-30

Practice – Page 30, #45-54

Cyclic Aliphatics and Aromatics

Cyclic Aromatics

• Hydrocarbon chains that form _______________

• A ring of three or more carbons connected by single bonds is called a _____________ alkane or a cycloalkane.

• Cyclic alkanes have ________ less hydrogen atoms than their corresponding continuous-chain alkanes.

• The general formula for a cyclic alkane is CnH2n which is the same as the general formula for an alkene that has one double bond.

• Cyclic alkenes are rings that possess a double carbon to carbon bond. They are sometimes referred to as __________________.

• All insoluble except for cyclopropane.

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• Add the prefix “cyclo” to the alkane name.

• Reading: Page 31-35

• Problems: Page 34 - #55-64

Aromatic Hydrocarbons

• Contains a ____________ ring

• Very stable, liquid at room temp, strong odours.

• Bonds are intermediate between double and single bonds due to delocalized electrons – ___________________________________

• Benzene is the root if side groups have 6 or fewer carbons.

• If the benzene ring is attached to a chain with 7 or more carbons, the ring is a side group and is referred to as a “________________” group.

• Use same rules as with other hydrocarbons.

___________________________

____________________________________

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• Reading: Page 35-39

• Problems: Page 38: #65-74

Hydrocarbon Derivatives

Compound consisting of a hydrocarbon with one or more functional groups attached.

Alcohols

Defined by the functional group called _________________ (-OH).

The general formula for an alcohol is R-OH where R represents an alkyl group.

Physical Properties

Small – ______________

Larger – non-polar

Higher bp than corresponding alkanes

Alcohols with fewer than 12 carbons are liquids at r.t.

Toxic!

Naming

End in –ol

Count to find the number of carbon atoms in the longest continuous chain (the alkyl stem).

Name the continuous chain of carbons in the same way you would name a corresponding alkane.

Change the -e ending of the alkane name to -ol.

Indicate the location(s) of the hydroxyl group(s) using the lowest possible number. Insert the number(s) into the suffix “butan-2-ol or pentane-2,3-diol”.

If the alkyl group is branched, priority in the numbering of the parent goes to the location of the hydroxyl group.

Write the IUPAC names that correspond to these structural formulas.

The longest chain is four carbons long, so the structure is derived from butane. The location of the hydroxyl group has to be assigned the lowest possible number - in

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this case the hydroxyl group is located on carbon #1. The name of the compound is ________________________________.

The longest chain is four carbons long, so the structure is derived from butane. There is a hydroxyl group located on carbon #2 (lowest possible number), so the name of the compound is _____________.

____________________________________

_____________________________________________

Priority for numbering goes to the location of the hydroxyl group. Alkyl groups have secondary importance in the naming scheme.

Draw a structural formula for each alcohol.

a. 2-propanol

First you draw the structure that corresponds to the alkyl prefix prop.

Then, based on the number in the name 2-propanol, you add the hydroxyl group to carbon #2.

b. 3-pentanol

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c. 2-methyl-2-butanol

Alcohols: Two Special CasesCompounds that possess more than one hydroxyl group are called polyalcohols. Example: enthane-1,2-diolThe suffixes –diol and –triol are added to the name to indicate two and three –OH groups.

Decompose the name from right to left.

diol means two hydroxyl groups

ethane means two single bonded carbon atoms

1,2 means the hydroxyl groups are located at carbons 1 and 2

Reading: Page 42-46 Problems: Page 34: #75-84

Haloalkanes

a compound that contains one or more ______________ atoms as part of its molecular structure.

many important uses including: fire retardation anaesthesia plastics manufacturing refrigeration/cooling systems

Physical Properties

Small – slightly soluble, most are insoluble Higher bp than corresponding __________________.

Naming

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The Halogen names are shortened and –oro is used as an ending. Eg. Fluoro, chloro, bromo, etc.

Identify and name the longest continuous chain of carbon atoms. Identify and name the halogen substituent(s). Assign lowest possible numbers to the

substituents. (If there are alkyl groups, these have priority in numbering) List the substituents in alphabetical order using appropriate prefixes. Write the full name of the compound beginning with the names of the substituents and

ending with the name of the parent.

Examples

The parent is propane. It has chlorine substituents at carbons #1 and #3. The name of the structure is_____________________.

The parent is ethane. In alphabetical order, the substituents are two chlorine atoms at carbon #1 and two fluorine atoms at carbon #2. The name is _______________________

___________________________________

Write a structural formula for 1-chloro-1,2-difluoroethane.

Reading: Pages 46-49 Problems: Page 49: #85-95

Aldehydes

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Contain a terminal carbonyl group (-C=O). This means the carbonyl is at the ____________ of the molecule.

Physical Properties

Bp lower than corresponding _______________ Most are liquids at r.t. Those with greater than 14 Carbons are waxy _________________. Small=soluble, greater than 7 C = insoluble.

Naming

Identify the longest continuous chain of carbon atoms (including the carbon atom in the carbonyl group). Note that the carbonyl carbon is designated as carbon #1 - this is a very important point!

Write the name of the corresponding alkane and replace the -e ending of the alkane name with -al.

Note that the carbon of the carbonyl group is counted as part of the carbon chain for naming purposes. AND there can be alkyl groups.

Examples:

_________________

___________________________

___________________________

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__________________________________

Reading: Pages 50-53 Practice: Page 52 - #96-105

Ketones

also contain the functional group called ____________________ unlike the aldehydes, the carbonyl group in ketones is located on a ________________ carbon. general formula for ketones is R–CO–R'.

Physical Properties

Similar bp to _______________________ Smaller than 15 C are liquids, larger are waxy solids.

Naming

1. Identify the longest continuous chain of carbon atoms (including the carbon atom in the carbonyl group).

2. Write the name of the corresponding alkane and replace the -e ending of the alkane name with -one.

3. If the carbon chain is five carbon atoms or longer, indicate the position of the carbonyl group by assigning it the lowest number possible.

Examples

____________________________

_______________________________

_____________________________________

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_________________________________________

Reading: Pages 53-57 Problems: Page 56: #106-115

Carboxylic Acids

Organic acids are common. The one you are probably the most familiar with is ethanoic acid which is also known as acetic acid or simply vinegar and fatty acids

Carboxylic Acids

The functional group that gives organic acids, also known as carboxylic acids, their chemical and physical properties is the __________________ group, -COOH. 

You can think of a carboxyl group as a carbonyl group and a hydroxyl group rolled into one.

     +            =     

The general formula for the carboxylic acids is RCOOH where R represents a __________________ atom or alkyl group. 

Unlike carbonyl and hydroxyl groups, carboxyl groups are always terminal. The carbon atom of the carboxyl group is considered to be part of the alkyl stem.

Naming Carboxylic Acids

To name a carboxylic acid when given a structural formula:

1. name the longest continuous chain of carbons, including the carbon of the carboxyl group, using an alkane name. The carbon atom in the carboxyl group is carbon #1.

2. if present, list the names of any alkyl branches and assign each a number. Build the name as you would for a branched hydrocarbon.

3. replace the -e ending of the hydrocarbon name with the suffix -oic.

4. add the word acid to the first name to make a phrase.

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Example

a. _______________________________

b. _______________________________

________________________________________

______________________________________

Reading: Pages 57-61 Practice: Page 61 - #116-125

Esters

Esters are abundant in nature. Many of the pleasant odours you associate with flowers and berries are due to esters as are the scents of bath oils, shampoos, soaps, and room fresheners, etc.

If you see "artificially flavoured" on the packaging of your favourite snack or candy, chances are that the flavour is due to a synthesized ester.

The functional group of an ester is actually a combination of a _____________ group from an organic acid and an ether link from an alcohol.

Esters are produced by reacting carboxylic acids with ___________________________.

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The general formula of an ester is RCOOR' where R represents hydrogen or a carbon chain/alkyl group and R' represents an alkyl group.

Naming Esters

1. count to find the number of carbon atoms in the -OR' component of the structural formula (the part derived from an alcohol) and assign it an alkyl group name.

2. count the number of carbon atoms in the R-C=O component of the structural formula (the part derived from the carboxylic acid) and assign it an alkane name with an -oate ending in place of the -oic ending.

3. combine the names to make a phrase.

Example

a. The -OR component of the molecule is propyl. The R-C=O component is derived from propanoic acid so its name is propanoate. The two names are combined to give _________________________________.

b. _____________________________________.

________________________________________

________________________________________

Reading: Pages 61-65 Practice: Page 65: #126-135

Ethers

Used as the first ___________________________ for surgery

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Oxygen atom single bonded to 2 carbons. R-O-R’ = alkoxy group

Physical Properties

Flammable Slightly __________________ 2-3 carbon – gas, larger - liquid

Naming

count to find the number of carbon atoms in the R group of the structural formula (the part bonded to the O) and assign it an alkane name. This is the root.

count the number of carbon atoms in the R’ component of the structural formula (the alkoxy group) and assign it an alkane name with an -oxy ending in place of the -ane ending. Indicate the location on the main chain with a number. This is the first part of the prefix.

Identify any side chains and include them as the 2nd part of the prefix. combine all three to name the compound.

1. Name these ethers :

a. ___________________________

b. ___________________________

c. ___________________________

Reading: Pages 66-70

Practice: Page 69: #136-146

Amines

You might recall that esters tend to have pleasant scents. Well, the same cannot be said for amines and amides. Their scents are characteristically unpleasant. ___________ is one of many common examples.

Amines are derived from ammonia (NH3)

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The functional group is one hydrocarbon group bonded to an _______________ group (-NH2). These amines have the general formula RNH2 where R represents an alkyl group.

To name an amine, identify the alkyl group and add the suffix -amine to its name.

Example

______________________________

_______________________________

Reading: pages 70-74

Practice: Page 74: #147-158

Amides

The functional group of an ____________ consists of a carbonyl group and an amino group.

An amide can be produced by reacting a carboxylic acid with ____________ (NH3).

The general formula RCONH2 where R represents hydrogen or an alkyl group.

To name an amide, write the name for the carbon chain containing the carbonyl group, drop the -e ending, and add the suffix -amide.

Note: Unlike Amines, we do not name the carbons as alkyl groups, but as alkanes.

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Example

__________________________

__________________________________

Reading: Pages 75-80 Practice: Page 79: #159-169

Summary of Polarity

Amide>acid>alcohol>ketone=aldehyde>amine>ester>ether>alkane

Priority of Functional Groups in Naming = Appendix B (page 730).

Organic Reactions

Addition

• Involves alkenes and ___________________• Atoms are added to the double or triple bond• Reactant is often water, hydrogen or halogen.• To understand which product will form when isomers are possible, use Markovnikov’s Rule: H

will attach to the C already bonded to the most H atoms.

• Reading: Pages 96-99• Practice: Page 99: #1-6

Elimination

• Atoms are removed and ____________________ bonds formed• Reverse of addition• Eg. Alcohol à alkene + Y-Z (in presence of strong acid)• Eg. Haloalkane à alkene (in presence of strong base)

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• Reading: Pages 100-102

• Practice: Page 102: #12-16

Substitution

• H or functional group replaced by another

• Mainly alcohols and ___________________ involved

• Alcohol + acid à haloalkane + water

• Haloalkane + OH- à alcohol + anion

• CH3-CH2-OH + HCl à CH3-CH2-Cl + H-OH

• Ethanol + hydrogen chloride à chloroethane + water

• Reading: Pages 103-104

• Practice: Page 104: #24,26-28, 31

Condensation

• 2 large molecules react to form a larger molecule + ________________

• Carboxylic acid + amine à amide + water

Esterification

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• Special type of _______________________

• Carboxylic acid + alcohol à ester + water

Hydrolysis

• Reverse of ________________________

• Water is used to break bonds

• Reading: Pages 105-108

• Practice: Page 108: #33-42

Oxidation and Reduction

• Oxidation: carbon forms __________ bonds to Oxygen and fewer to Hydrogen.

• Eg. Alcohol à aldehyde or ketone OR aldehyde à carboxylic acid

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• Reduction: carbon forms _________________ bonds to Oxygen and more bonds to Hydrogen.

• Eg. Aldehyde or ketone à alcohol OR alkene à alkane

• Reading: Pages 109-110

• Practice: Page 113: #43-48

Polymer Equations

• Polymer: a large molecule made up of repeating ________________ (monomers)

• Eg. Proteins, carbohydrates, plastics, chewing gum.

• Addition Polymerization

– Alkene monomers joined to form a polymer

– Named for the monomer

– Eg. Polystyrene, polyacylamide, polyethene.

• Condensation polymerization

– Monomers joined through condensation

– Water is usually formed

– Each monomer has 2 functional groups

– Joined by a ester or amide linkage

• Reading: Pages 116-126

• Practice: Page 121: #53-58