What is Organic Chemistry? Theobromine- found in chocolate

Essential Questions: What is organic chemistry? What are some unique characteristics of carbon? Organic Chemistry: 1. Study of carbon and compounds containing carbon 2. Number of organic compounds is much more that the number of inorganic compounds (does not contain C). 10,000 new ones discovered each year. Hydrocarbon-organic compounds that contain only atoms of carbon and hydrogen, Exs: alkanes, alkenes, alkynes

What is a hydrocarbon?  Hydrocarbons are made up just of carbon and hydrogen.  Methane, CH 4, is the simplest.

CARBON is the center of Organic Chemistry This is C protons 6 neutrons 6 electrons 4 valence electrons Always makes 4 bonds.

Carbon- infinite bonding possibilities: Carbon frequently bonds with hydrogen (yellow) and/or with oxygen (red).

Diamonds are pure carbon.  The carbons are joined just to other carbons.  Each C joined to 4 others.  Very strongly bonded.  Example of a NETWORK SOLID.  High m.p., nonconductor

Bonding of carbon atoms: HHHHas 4 valence electrons  F F F Forms 4 covalent bonds CCCCan form a single, double, or triple covalent bond. EEEEach carbon atom is in the center of tetrahedron. Single Covalent Bond-shares 1 pair of electrons Double Covalent bond-shares 2 pair of electrons Triple Covalent Bond- shares 3 pair of electrons

Organic compounds have the following properties: LLLLow melting point LLLLow solubility in water (they are nonpolar) NNNNonelectrolytes CCCCovalent bonds SSSSlower reaction rates WWWWeak intermolecular forces

Saturated –organic compounds with only single covalent bonds. Unsaturated Compounds – compounds that contain double or triple covalent bonds.

Basic hydrocarbons:  The first four have all single bonds  All single bonds  SATURATED  Saturated  end in - ane  Containing a multiple bond  Unsaturated.

Essential Questions: What are the types of hydrocarbons? What are the characteristics of each type? Types of hydrocarbons  Alkanes  Alkenes  Alkynes

All are classified as a homologous series * Homologous series -is a group of related compounds in which each member differs from the one before it by the same additional unit.

1. Alkanes: NNNNonpolar molecules LLLLow molar mass HHHHave weak Van der Waals Forces TTTTend to be gases or liquids that have a low BP HHHHydrocarbon in which there is only single covalent bonds TTTTends to release energy when burned WWWWhen the number of carbon increase in the series, the B.P increases GGGGeneral formula is: Cn H 2n+2 EEEEnd is ane. Exs. pentane and hexane TTTTable Q

Methane (CH 4 )- make up 90% of natural gas Ethane (C 2 H 2 )- accounts for the rest of natural gas Propane (C 3 H 6 )- used for home heating fuel, grills, camping equipment Butane (C 4 H 10 )- used in disposable lighters Other membranes of the alkanes:  Pentane C 5 H 12  Hexane C 6 H 14  Heptane C 7 H 16  Octane C 8 H 15  Nonane C 9 H 20  Decane C 10 H 22  Prefix is based on number of carbons  Table P

Single bonded hydrocarbons…  Saturated  Called ALKANES  Have general formula: C n H 2n+2  Since same formula, they are part of a homologous series  Table Q

Alkene: Unsaturated hydrocarbons Unsaturated hydrocarbons Contain double covalent bonds Contain double covalent bonds End in ene End in ene Ex: ethene, propene .General Formula: Cn H2n

Sometimes we have double bonds…  Series is called alkenes  General formula: C n H 2n  Unsaturated (contain a multiple bond)

First Three Members of the alkenes:  Ethene C 2 H 4  Propene C 3 H 6  Butene C 4 H 8

Alkynes:  Unsaturated hydrocarbons  Contains triple covalent bond  End in yne Ex: propyne, butyne  General formula :C n H 2n-2 Ethyne  Also known as acetylene  Fuel use in welding torches

Sometimes we have a triple bond… Alkynes GGGGeneral formula: CnH2n-2 UUUUnsaturated

 Hydrocarbons can be straight chained, branched or cyclical Straight Chain Ex: Butane  Branched 2-methyl propane  Cyclical Ex: benzene

Essential Questions: What are isomers? What are the characteristics of isomers? Isomers: 1. Compound that have same molecular formula, but different structure. 1. Compound that have same molecular formula, but different structure. 2. Have different physical and chemical properties 3. As the numbers of carbons in a compound increase, so does the number of possible isomers

What are isomers? Same atoms, different structure: Butane methyl propane C 4 H 10 1-hexenecyclohexene C 6 H 12

Let’s try more… Both are butene- how can I distinguish them? Same formula but different structures- these are ISOMERS!!

How to name hydrocarbons:  Identify the longest carbon chain  Identify whether hydrocarbon is alkane (single bonded), alkene (double), or alkyne (triple).  Name will be root plus suffix. 3 carbon chain  prop- Single bonds  - ane PROPANE

Sometimes we have branched hydrocarbons…  One carbon branch (CH 3 -) = methyl  Two carbon branch (CH 3 CH 2 -) = ethyl  2-methyl pentane  3-methyl pentane

Sometimes we have multiple branches…  2,2-dimethyl-3- ethylpentane  2,2-dimethyl pentane  Use di-,tri-, … for identical branches.

Cyclic Hydrocarbons-A hydrocarbon chain that is formed in a ring. Aromatic Hydrocarbon: 1. An organic compound that contains a benzene ring (C 6 H 6 ) or other ring in which the bonding is like benzene. 2. Class of compounds responsible for aromas of spices. Exs: ginger, cloves, vanilla, etc. Benzene In benzene, the bonding electrons between carbon atoms are shared evenly around the ring. Toluene- a compound with a benzene ring with an attached methyl group

Sometimes the carbons link up to form rings:  Cyclopentane  All single bonds  Cyclohexane  All single bonds

More rings !!  benzene toluene Phenol (benzene ring abbreviated)

Essential Question: What is distillation? Fractional Distallation: 1. Process used to separate components of crude oil. Exs. Kerosene, fuel oil, gas, etc. 2. Based on differences in BP 3. Column is hotter are the bottom, thus the substance with the highest BP condenses near the bottom.

Essential Questions: What are functional groups? What are the formulas for each group? Functional Groups:  Halides (Hydrocarbons)  Alcohols  Aldehydes  Ketones  Ethers  Organic Compounds  Esters  Amines  Amino Acids  Amides

Alcohols: a. Organic compounds in which one or more hydrogen atoms of a hydrocarbon are replaced by an OH- group(hydroxyl group). b. OH (hydroxyl group) gives alcohols their specific chemical and physical properties. c. Are non-electrolytes-do not ionize in water. d. Do not turn indicators colors. e. Are polar molecules, thus soluble in water

Alcohols:  Alcohols contain – OH, a functional group.  The functional groups gives them away.  See table R for functional groups Ethanol ↓, methanol ↑

Primary: a. Represented by: ROH or R-CH2-OH b. Alcohols can also be classified by the number of hydroxyl groups that are attached to the carbon chain. MMMMonohyroxy – 1 hydroxyl group DDDDihydroxy – 2 hydroxyl groups TTTTridhydroxly-3 hydroxyl groups

Essential Question: What is the difference between primary, secondary and tertiary alcohol? Types of Alcohols: 1. Primary 2. Secondary 3. Tertiary  Classified according to the carbon at which the OH group is attached.  Alcohols end in ol.

Name that alcohol…  2-butanol  ethanol

Halides(Hydrocarbons): a. Occurs when any halogen (F,Cl, Br or I) replaces a hydrogen atom in an alkane b. Often used as organic solvents c. Found in some pesticides.

3. Aldehydes: 1. When an oxygen atom is attached to a carbon chain by a double covalent bond called a carbonyl group(-C=0). General formula is RCHO General formula is RCHO Named by substituting al in place of the final e of the corresponding alkane name Named by substituting al in place of the final e of the corresponding alkane name

Aldehydes-  Ethanal  2 carbons = eth-  CHO functional group = al ending.

Ketone- an organic compound in which the carbon of the carbonyl group (C=O) is joined by 2 other carbons General formula – RCOR General formula – RCOR Naming by replacing final e from the corresponding alkane name with one Naming by replacing final e from the corresponding alkane name with one Used as a solvent, very polar substance Used as a solvent, very polar substance

Ketone – hydrocarbons connected by C=O  Propanone (acetone)

Another aldehyde and ketone…

Aldehyde and Ketone

Ethers: a. Series of organic compounds in which two carbons chains are joined by an oxygen atom bonded between two carbon atoms a. Series of organic compounds in which two carbons chains are joined by an oxygen atom bonded between two carbon atoms b. General formula: b. General formula:

An ALCOHOL and an ETHER

ETHERS- hydrocarbons connected with an oxygen  Dimethyl ether  Diethyl ether  Methyl ethyl ether

Organic Acids: 1. A homologous series of organic compound whose functional group (COOH), a carboxyl group 2. Named by replacing the e on the hydrocarbon name with oic acid Exs: Ethanoic acid(vinegar)CH 3 COOH Propanoic acid CH 3 CH 2 C00H

Organic acid- COOH on end of hydrocarbon.  Ethanoic acid (acetic acid)  Propanoic acid

Esters: 1.General formula R-CO-OR (The R-COOH comes from an organic acid and the R comes from an alcohol) 2. Have strong fragrant aromas and are responsible for the odors of many foods and flavoring. Ex: wintergreen, pineapple 3.Named by using the alkyl name of the alcohol followed by the acid group modified to end in oate Exs: Methyl Ethanoate and Ethyl Ethanoate

Ester – Oxygen in the chain and off the chain. Ethyl propanoate Name is short chain plus long chain plus “oate”.

Amines: 1. When one or more hydrogens atoms of ammonia (NH 3 ) are replaced by an alkyl group 2. The e ending of an alkane is changed to end in amine and the alkane chain is numbered to show the location of the amine group

Amine- N in the chain.  Pentanamine  Name is Prefix + amine  No number required

Amide – N in the chain and O off the chain.  Name is “hydrocarbon root + amide”  Ethanamide   Butanamide 

Amino Acids: 1.Contains a carboxyl group (COOH) and a amine group 2.Amino group is attached to the C atom that is adjacent to the acid group Ex: alanine 3.Ten essential A.A that the body must obtain through diet 4.Building blocks of proteins Amides- formed when one hydrogen atom of the amino group reacts with the OH- of the organic acid

Essential Questions: What are the different type of organic reactions? What is the chemical reaction of each type?  Types of Organic Reactions:  1. Combustion  2. Substitution  3. Addition  4. Esterification  5. Saponification  6. Fermentation  7. Polymerization

Combustion- most common type of organic reaction Complete combustion – carbon dioxide is produced Complete combustion – carbon dioxide is produced Incomplete combustion – carbon monoxide is produced Incomplete combustion – carbon monoxide is produced

Substitution- Replacement of one or more H atoms in a saturated hydrocarbon with another group or atom

Addition: a. Adding one ore more atoms at a double or triple bond b. Unsaturated hydrocarbon can also react with hydrogen by addition reactions

Etherification: a. A reaction between an organic acid and an alcohol b. Produces an ester and water b. Produces an ester and water

Sponification – one ester reacts with an inorganic base to produce an alcohol and a soap Fermentation- process in which yeast cells secrete the enzyme zymase to break down glucose

Fermentation

Polymerization- process by which a polymer is made Ex: plastics, rayon, nylon, polyethylene, proteins, starches Polymer- chain of repeating units of monomers Polymer- chain of repeating units of monomers

Two Types of Polymerization: 1. Addition Polymerization 2. Condensation Polymerization Addition Polymerization: a. Involving the joining of monomers of unsaturated compounds. b. General formula: nC 2 H 2  (C 2 H 2 )n Condensation Polymerization – Results from the bonding of monomers by removal of water from the hydroxyl groups and joining the monomers by an ether or ester linkage (Dehydration synthesis).