Section B:

Organic Molecules

1. The branch of chemistry that deals with molecules that contain carbon (i.e. organic molecules). 2. Organic molecules range in size from simple molecules to complex structures containing thousands of atoms. 3. Although C is present in all organic molecules, other elements such as H, O, N, S and P are also common.

1. Main source CO2 in the air, utilized mainly during the process of photosynthesis: 6CO2 + 6H2O + energy from sunlight C6H12O6 + 6O2 (all in the presence of chlorophyll). 2. Fossil fuels (formed from the decaying remains of dead organisms) coal, petroleum and natural gas.

1. Carbon has : 4 valence electrons (all involved in bonding) and forms predominant covalent bonds. 4 bonds from every carbon atom single bonds (sigma bonds) double bonds (pi bonds) triple bonds (a combination of pi and sigma bonds) the ability to form long chain structures through the linking together of C atoms, the chains can be either branched or unbranched.

Hydrocarbons (only contain H and C)

Aliphatic Hydrocarbons

Aromatic Hydrocarbons

Acyclic Compounds (straight/chain structures)

Cyclic Ring Structure

Benzene Ring

Alkanes (all single bonds) Alkenes (at least 1 double bond) Alkynes (at least 1 triple bond) bonds)

Cycloalkanes

Section B: Organic Molecules

Section B:

Organic Molecules

Method: Molecular formula

Explanation: Shows how many atoms of each element are in a molecule. The number of each atom is written as a subscript after the atomic symbol. Shows every bond (represented by a line) between every atom in the molecule.

Example: (2-methylpropane) C4H10

Structural formula

Condensed structural formula/semi-structural formula

Each C atom and the H atoms bonded directly to it are listed as a molecular formula, followed by a similar molecular formula for the neighboring C atom. Branched groups are indicated in brackets after the C atom to which they are bonded.

CH3CH(CH3)CH3 or CH3-CH(CH3)-CH3

1. 2.

Identify the functional group of the compound which will determine the suffix of the name. Find the longest continuous carbon chain (straight or branched) and allocate its prefix according to the number of carbon atoms in the chain. Number the longest carbon chain double and/or triple bonds take priority over branched groups. i. If there are only single bonds, start at the end nearest the first branched group, so that the carbon atom bonded to the branched group receives the lowest possible number. ii. If there are double or triple bonds, start numbering the carbon atoms so that these bonds receive the lowest possible numbers. iii. Multiple bonds of the same type are indicated by means of a prefix (di-, tri-, tetra- etc.). iv. If both types of bonds are present, they are also listed alphabetically (i.e. -ene before -yne). Name the branched group according to the number of carbon atoms it has, and give a number according to where it is located on the longest carbon chain. i. If there is more than one branched group of the same kind, the prefixes di-, tri-, tetra-, penta- etc. are used to show the presence of these additional groups. ii. If there are 2 branched groups on the same alpha carbon, the number of that carbon is written twice. iii. If multiple branched groups are not identical, write them in alphabetical order. (the prefix of the branched group (e.g. di- in dimethyl) is ignored and the first letter of the branched group name is taken into consideration. (e.g. m in dimethyl).). iv. Numbers and letters are separated by hyphens (-) and numbers are separated by commas (,). If the name of the organic molecule has numerical values in between it, always ensure that that the letters preceding and succeeding it are a vowel and a consonant e.g. butan-1-ol. (N.B. the same applies to prefixes, which are not considered butan-1,2-diol)

3.

4.

5.

Section B: Organic Molecules

Section B:
Hydrocarbons: Group Suffix: Name: Alkanes -ane

Organic Molecules
Functional Group: Example: Number of Carbon Atoms 1 2 3 4 5 6 7 8 9 10 Alkyl Group Structure CH3 CH3CH2 CH3CH2CH2 CH3CH2CH2CH2 Prefix

Alkenes

-ene

Alkynes

-yne

methethprobutpenthexheptoctnondecAlkyl Name methyl ethyl propyl butyl

Hydrocarbon Derivatives: Group Name: Alcohols Suffix: -ol Functional Group: Example:

Carboxylic Acids Esters

-oic acid

-oate

Aldehydes

-anal

Ketones

-one

Ethers Haloalkanes

ether Prefix: flouro- (F) chloro- (Cl) bromo- (Br) iodo- (I) amide

Amides

Amines

amine

Section B: Organic Molecules

Section B:

Organic Molecules

Bond Nature and Reactivity

Only contain single

covalent bonds between their C atoms Saturated compounds Quite unreactive compared to other chemical species.

Contain at least one double

bond Unsaturated compounds More reactive than alkanes

Contain at least one triple

bond

Unsaturated compounds Highly reactive compared

to alkanes

Density Solubility

Generally less dense than water (1 g.cm-3) able to float. Non-polar covalent molecules: insoluble in water and other polar solvents soluble in non-polar solvents. Non-polar covalent molecules: slightly soluble in polar solvents

soluble in non-polar solvents.

Boiling and Melting Points and Volatility

Weak van der Waals intermolecular forces Boiling and melting points increase as molecular size (and therefore surface area and the
strength of intermolecular forces) increases.

The more branched a molecule is, the lower the boiling point will be (surface area is decreased
so there are less van der Waals forces between adjacent molecules).

The greater the intermolecular forces, the less the volatility. Miscellaneous Compounds with 5 or more
C atoms are liquids at room temperature (4 or less are gases). Isomers molecules with the same molecular formula but different structural formula. Paraffins

Compounds with 5 or more C

atoms are liquids at room temperature (4 or less are gases). Geometric isomers molecules with the same molecular and structural formula, but which differ in spatial orientation. Olefins (oil-forming) Can be made by cracking an alkane i.e. heating a longchain alkane in the presence of a catalyst so that it breaks into smaller molecules.

Acetylenes

1. Boiling and melting points: increase as the number of carbons increase NOT entirely due to increased molecule size, but also due to the fact that halides can make the molecule polar, and the intermolecular forces become van der Waals dipole-dipole forces. 2. Polarity and solubility: As a whole, the molecule is not very polar, only slightly and mainly in the area where the halogen ion is do not form hydrogen bonds with water (i.e. they are insoluble in water) 3. Boiling point is also affected by the size of the halogen ion (i.e. the boiling point of 1-chloroethane is less than that of 1bromoethane). 4. Often used as solvents e.g. trichloromethane (chloroform).

1. Alcohols with 4 or less carbons are water soluble, because the chain is short and does not impact negatively on the polar OH bond.

Section B: Organic Molecules

Section B:

Organic Molecules

2. The hydroxyl (OH) group causes hydrogen bonding with other polar molecules and water. 3. Branched alcohols are also relatively soluble in polar solvents. 4. In alcohols with more than 4 carbons, the alkyl non-polar group dominates and the molecule as a whole becomes insoluble in polar solvents. 5. Alcohols can be very volatile, but the addition of strong hydrogen bonds decreases the volatility. 6. The boiling points of alcohols can be as much as 100OC greater than that of comparable alkanes.

1. The hydrogen of an alcohol is replaced by a carbon chain less polar, therefore less soluble in polar solvents. 2. Boiling points are higher than those of hydrocarbons but less than those of alcohols due to the very electronegative oxygen.

1. Contain a carbonyl group (C=O) this increases the intermolecular forces and the boiling points are higher than those of hydrocarbons and ethers, but lower than those of alcohols.

1. Carboxylic acids contain a carboxyl group (COOH) the molecule becomes much more water soluble due to 2 possible hydrogen bonding sites. 2. The length of the hydrocarbon chain does not affect the solubility, and molecules with 10 or more carbons are completely insoluble. 3. Boiling points are higher than corresponding alcohols. 4. They are weak acids that occur freely in nature. 5. Esters contain a carbonyl group (C=O) and have lower boiling point than the acids due to a carbon chain replacing the hydrogen. 6. Smaller esters are very soluble in water, but as the molecule size increases, so does the insolubility.

1. Aromatic compounds have strong, characteristic smells and many of these have a ring structure with alternating double and single bonds (i.e. a conjugated ring structure). 2. Aromatic compounds are very stable, and their molecules are carcinogenic. 3. Only single bonds cycloalkanes, each with 2 less hydrogen atoms than a comparable alkane chain (general formula: CnH2n). 4. The prefix cyclo- is added to the common alkane name, and the numbering is so that all attached chains have the lowest possible number. 5. When naming cycloalkenes (arenes), the double bond is also given the lowest possible number. 6. These compounds are the basis of the fuels used in combustion engines and are produced by cracking alkane chains (some cyclic, some not). 7. Benzene is a 6 carbon chain with 3 alternating double and single bonds 1,3,5-tricyclohexene.

Non-polar Molecules: 1. Alkanes 2. Alkenes 3. Alkynes 4. Cyclohydrocarbons 5. Amines

Polar Molecules: 1. Carboxylic acids 2. Alcohols (chains with 4 carbons or less) 3. Ketones 4. Aldehydes 5. Ethers 6. Amides

1. Hydrogen bonding: takes place in alcohols and carboxylic acids as a result of the hydroxyl group (OH). 2. Van der Waals forces: take place in hydrocarbons and the nitrogen containing molecules.

Section B: Organic Molecules

Section B:

Organic Molecules

3. Londen forces (momentary dipole): take place between the molecules which are gases and also non-polar covalently bonded molecules.

1. Increases boiling point. 2. Makes the substance more water soluble, especially if a OH group is present hydrogen bonding. 3. If a carbonyl group is present, 2 hydrogen bonds can form between neighboring molecules i.e. there are 2 possible sites where hydrogen bonding can occur.

1. When burnt, the substance readily reacts with excess O2 present in the air, and H2O and CO2 are produced. 2. Heat is given off (i.e. an exothermic reaction). e.g. CH4 + 2O2 CO2 + 2H2O + energy C3H8 + 5O2 3CO2 + 4H2O + energy 2C2H2 + 5O2 4CO2 + 2H2O + energy

1. The process in which unsaturated compounds produce saturated compounds. 2. Saturated compounds readily react with H2, H2O and the halogens - a double (or triple) bond breaks, and the other atoms are added to the chain. 3. Addition reactions happen faster that substitution reactions this difference in rate can be used to test whether a hydrocarbon is saturated or unsaturated. 1. Hydrogenation: 1. Hydrogen (H2) is added to an unsaturated hydrocarbon in the presence of a suitable catalyst (e.g. Pt, Pd or Ni). 2. The process is often used to solidify liquid hydrocarbons. 3. Vegetable oils containing double bond (unsaturated fat) are hardened through hydrogenation the oil is made more saturated. e.g. CH2=CH2 + H2 CH3-CH3 (in the presence of a Pt catalyst) Hydration: 1. Water (H2O) is added to an unsaturated hydrocarbon in the presence of a strong acid as a catalyst. (e.g. conc. H2SO4). 2. The H atom attaches itself to the carbon with the most hydrogens, while the OH group attaches itself to the most substituted carbon. 3. An alcohol is formed as a result. e.g. CH2=CH2 + H2O CH3-CH3-OH (in the presence of a H2SO4 catalyst)

2.

1. The process in which saturated compounds produce unsaturated compounds. 1. Dehydration of alcohols: 1. A H2O molecule is eliminated in the presence of strong acid and heat, to produce an alkene. 2. If more than one elimination is possible, the reaction will take place at the carbon with the least hydrogens. e.g. CH3CH2OH CH2=CH2 + H2O (in the presence of an acid catalyst and heat) CH3-CH2-CH2-OH CH3-CH=CH2 + H2O (in the presence of an acid catalyst and heat)

Section B: Organic Molecules

3.

Hydrohalogenation: 1. A hydrogen halide (e.g. HBr) is added to an unsaturated hydrocarbon (no water may be present). e.g. CH2=CH-CH3 + HBr CH3-CBr-CH3 (C3H6 +HBr C3H7Br) CH2=CH2 + HCl CH3-CH2Cl (C2H4 + HCl C2H5Cl)

Section B:
2.

Organic Molecules

Dehydrohalogenation: 1. A haloalkane reacts with a strong hydroxide (e.g. KOH) to produce an alkene, metal halide (acid) and H2O e.g. CH3-CH2-CH2Br +KOH CH3=CH-CH2 + KBr + H2O (C3H7Br +KOH C3H6 + KBr + H2O)

3.

Cracking: 1. In the petroleum industry, longer C chains mean higher boiling points. 2. To solve this, long chains are broken up into smaller chains with/without many branches. 3. The reaction conditions are either: High pressures and temperatures with no catalyst (thermal cracking) Low pressures and temperatures with a catalyst (catalytic cracking) e.g. CH3CH3 CH2=CH2 + H2 (at a high temperature)

1. The process in which a hydrogen atom or a compound is replaced by a halogen atom or nitrogen-oxygen group. 2. Energy in the form of heat () or sunlight (hf) is necessary for substitution reactions to take place (as alkanes are very unreactive). 1. Halogenation: 1. A hydrogen atom is displaced by a halogen atom producing a haloalkane and an acid. 2. Haloalkanes are not found in nature and are often harmful chemicals. e.g. CH3-CH2-CH3 + Br2 CH3-CH2-CHBr + HBr (in the presence of or hf).

1. 2. 3.

Primary alcohol: a hydroxyl group is attached to a single carbon atom. Secondary alcohol: a hydroxyl group is attached to a carbon atom which is attached to 2 other carbon atoms on either side. Tertiary alcohol: a hydroxyl group is attached to a carbon atom which is attached to 3 other carbon atoms. Alcohols react with strong halide acid to form haloalkanes: e.g. a tertiary alcohol: C(CH3)3OH + HBr C(CH3)3Br +H2O (at room temperature) Primary and secondary alcohols need to be treated with conc. H2SO4 and NaBr. The first reaction is the formation of HBr, which then reacts with the alcohol to form the bromoalkane. CH3-CH2-OH +HBr CH3-CH2Br + H2O

Hydrolysis (reactions of bases with haloalkanes): 1. The haloalkane is dissolved in ethanol first then an aqueous solution of the base is added. 2. It can be done slower by adding water without the base. e.g. CH3-CH3Br + KOH CH3-CH3-OH + KBr Polymerisation: 1. Many short chains are combined to form long, complex chains. 2. A compound is able to add to itself when in the presence of a suitable catalyst, forming a polymer. e.g. Polyvinylchloride Esterification (reaction of an alcohol with a carboxylic acid to produce an ester): 1. Esters give a fruit or vegetable its characteristic scent - today, many esters are produced synthetically and used as flavourants in food. 2. During the reaction, H2SO4 is used as a catalyst. 3. The alcohol gives a hydrogen ion and the carboxylic acid gives off a hydroxyl ion. 4. Naming alcohol: -yl carboxylic acid: -anoate. Oxidation of Alcohols Esterification (reaction of an alcohol with a carboxylic acid to produce an ester): 1. An alcohol reacts with an oxidizing agent (i.e. oxygen), forming an acid. e.g. ethanol + oxygen ethanoic acid

Section B: Organic Molecules

Section B:

Organic Molecules

Dry Cleaning: 1. Many stains on fabrics are caused by organic molecules which do not have polar bonds insoluble in water. 2. Solvents used for such stains need to be non-polar covalently bonded substances. 3. CCl4 (tetrachloromethane) has been replaced by C2HCl3 (trichloroethene) as it was carcinogenic and produced CFCs. Saponification: 1. Soaps are made from long chains of carboxylic acid salts. 2. A long carboxylic acid chain is reacted with NaOH this causes a long non-polar chain with a polar head, making it able to dissolve in water but still cling onto fatty/oily substances. Common Names and Facts: 1. Single carbon chains are often given the prefix for- e.g. methanoic acid formic acid. 2. 2 carbon chains are often given the prefix acet- e.g. ethanoic acid acetic acid. 3. Ethene a natural substance produced by fruit during the ripening process. It is often used in ripening sheds to speed up the artificial ripening of produce. 4. Ethyne acetylene, which is used for welding. 5. 1,2,3-tripropanol glycerol.

Section B: Organic Molecules

Section B:

Organic Molecules

Section B: Organic Molecules