Organic Chemistry

1. Organic Chemistry

2. Organic Chemistry • The study of Carbon. • Carbon is in all living things. • Carbon is an extremely versatile elements and can bond with other carbon atom to make chains, rings, and vast networks creating countless numbers of compounds.

3. Carbon Bonding • A Lewis dot structure displays carbon having only 2 unpaired electrons in its ground state. • When Carbon bonds however, the paired electron can split apart and occupy separate orbitals, allowing carbon to form four covalent bonds. Carbon in its ground state Carbon in its bonded state

4. Carbon Bonding • Carbon can share its four unpaired electrons to make multiple covalent bonds when forming a chain. • Covalent Bond = bond formed by the sharing of electrons between two atoms. • Single Covalent Bonds – sharing of one pair of electrons between two carbon atoms. • Represented by a single line. • Double Covalent Bonds – sharing of two pairs of electrons. • Represented by a double line. • Triple Covalent Bonds – sharing of three pairs of electrons. • Represented by a triple line.

5. Carbon Bonding • Carbon is able to form many different compounds due to its unique bonding capabilities.

6. Properties of Organic Compounds Due to the nature of covalent bonds organics generally possess the following properties. • Low Melting Points • Low Boiling Points • Poor Conductors of Electricity • Non-Electrolytes • Poor conductors of Heat • Non-polar • “Like Dissolves like” • Slow Reaction Rates. Organic compounds that contain only single bonds are called Saturated. Organic compounds with one or more double or triple bonds are called Unsaturated.

7. Structural Formulas • Attempt to display the what the organic compound looks like. • Number of atoms • Identity of atoms • Bonds • General Shape Example: Molecular Formula C3H8 Structural Formula Condensed Formula; CH3CH2CH3

8. HydroCarbons • A homologous series of compounds that contain only hydrogen and carbon. • Homologous Series – a group of related compounds in which each member differs from the one before it by the same additional unit. • Form the backbone of most organic substances. • Categorized by the covalent bonds they possess. • Alkanes • Alkenes • Alkynes

9. AlKanes • Hydrocarbon series that possess only single covalent bonds between carbons. • Tend to release energy when burned. • Examples: • Homologous series (CH2) • Suffix: -ane • General Formula: CnH2n+2 Methane Ethane Propane

10. Alkenes • Hydrocarbon series where at least one double covalent bond is present between two carbons. • Used to make organic substances such as polypropyene. • Examples: • Homologous Series (CH2) • Suffix: -ene • General Formula CnH2n Ethene Butene Propene

11. Alkynes • Hydrocarbon series where at least one triple covalent bond is present between two carbons. • Used in welding. • Examples: • Homologous Series (CH2) • Suffix: -yne • General Formula CnH2n-2 Butyne Ethyne Propyne

12. Isomers • Compounds that possess the same molecular formula but have more than one structural formula. • Example: C4H10 • Despite having the same structural formula, isomer will exhibit very different chemical and physical properties. • The number of possible isomers increases as the number of carbon atoms increases. Butane Methyl Propane

13. Naming Organic Compounds • Find the longest carbon chain which contains the functional group or multiple bond if present and name it (using the correct ending). • Number the longest chain (left to right or right to left) so that the functional group/multiple bond/longest side chain (branch) is on the lowest numbered carbon possible. • Name each side group but change the ending to -yl. (Alkyl groups) • Use a prefix di-, tri-, tetra-, etc. to denote how many side groups of each length are present. • Before naming the side group give the number of the carbon to which the side group is attached. • Arrange the side groups in alphabetical order ignoring the prefixes di-,tri-, etc.

14. Naming Organic Compounds • Name this hydrocarbon…

15. Naming Organic Compounds • Find the longest carbon chain which contains the functional group or multiple bond if present and name it (using the correct ending).

16. Naming Organic Compounds • Number the longest chain (left to right or right to left) so that the multiple bond/functional group/longest side chain (branch) is on the lowest numbered carbon possible. The number of carbons determines the name of the parent chain. 6 carbons = hex = hexene

17. Naming Organic Compounds • Name each side group but change the ending to -yl. (Alkyl groups) 1 Carbon = methane, side group(alkyl group) = methyl

18. Naming Organic Compounds • Use a prefix di-, tri-, tetra-, etc. to denote how many side groups of each length are present. Only 1 methyl side group present.

19. Naming Organic Compounds • Before naming the side group give the number of the carbon to which the side group is attached. 2-methyl

20. Naming organic compounds • Arrange the side groups in alphabetical order ignoring the prefixes di-,tri-, etc. 2-methyl hexene Condensed Formula: CH3CH2CH2CH2CH(CH3)CH3

21. Functional Groups • Atoms or groups of atoms that attach to hydrocarbon chains. • Create whole new compounds each with their own distinct chemical and physical properties. • Halides • Alcohols • Adehydes • Ketones • Ethers • Organic Acids (COOH) • Amines • Amino Acids • Amides

22. Halides • One of the Halogens (Group 17) is attached to the hydrocarbon chain, replacing a hydrogen. • Organic Halide(Halocarbon) • Halides are named for the halogen present on the hydrocarbon chain with a number designating which carbon it is on. • F = flouro, Cl = chloro, Br = bromo, I = iodo Chloromethane CH3Cl 2,2,3-tricholorbutane CH3CCl2CCHClCH3

23. Alcohols • Compounds in which one or more hydrogen atoms on a hydrocarbon chain are replaced by an –OH group (Hydroxyl Group). • Does not form OH- ions in water. • Alcohols are non-electrolytes. • Alcohols are polar and are soluble in polar solvents such as water. • Suffix: -ol • Classification of alcohols • Primary • Secondary • Tertiary

24. Classification of alcohols • Primary Alcohol – has the hydroxyl group(OH) attached to a primary carbon at the end of the chain. • Represented by R-OHor R-CH2OH 1-butanol

25. Classification of alcohols • Secondary alcohol – has a hydroxyl group (OH) attached to a secondary carbon. • Represented by R-CH(OH)-R’ 2-butanol

26. Classification of Alcohols • Tertiary Alcohols – have a hydroxyl group (OH) attached to a tertiary carbon atom. • Represented by R1R2R3COH 2-methy, 2-propanol

27. Poly-hydroxy compounds • Some organic compounds contain more than on hydroxyl group. • Monohydroxy – an alcohol with one –OH group. • Suffix; -ol • Dihydroxy – an alcohol with two -OH groups. • Suffix; -diol • Trihydroxy – an alcohol with three –OH groups. • Suffix; -triol 1,2-ethanediol 1,2,3-propanetriol

28. Aldehydes • Hydrocarbons that contain a carbonyl group (-C=O) on a primary (end) carbon. • Suffix; -al Methanal Propanal

29. Ketones • Hydrocarbons that contain a carbonyl group (-C=O) on a secondary carbon (a carbon that is attached to two other carbons). • Suffix; -one Propanone

30. Ethers • Two carbons chains joined together by an oxygen atom between them. • R-O-R’ • Suffix; -yl ether dimethyl ether ethylmethyl ether

31. Organic Acids • Hydrocarbon chain with a carboxyl (-COOH) group attached. • R-COOH • Suffix; -oic acid methanoic Acid ethanoic Acid

32. Esters • Organic compounds with a generalized formula of; • R-CO-OR’ (where R’ is an alcohol and R is an acid) • Suffix; -yl (alcohol part) -oate (acid part) Ethyl ethanoate

33. Amines • Derivatives of ammonia. • Alkyl groups attach to the Nitrogen in place of a hydrogen on the ammonia (NH3) molecule. • suffix; -amine pent-2-amine

34. Amino Acids • Contain a carboxyl group as well as an amine group. • Building blocks of proteins. • 10 essential amino acids. Alanine

35. Amides • Compound formed by the combination of two amino acids during a condensation reaction.

36. Organic Reactions • Combustion Reactions • Hydrocarbons burn in the presence of sufficient oxygen to produce water and carbon dioxide. C3H8(g) + 5O2(g) 3CO2(g) + 4H2O(g) • Complete Combustion • If there is not enough oxygen present water and carbon monoxide (CO) will be produced instead. 2C3H8(g) + 7O2(g) 6CO2(g) + 8H2O(g) • Incomplete Combustion

37. Organic Reactions • Substitution • Involves the replacement of one or more hydrogens in saturated hydrocarbon with another atom or group. C2H6 + Cl2 C2H5Cl + HCl • Addition • Involve adding one or atoms at a double or triple bond. C2H4+ Cl2 C2H4Cl2 • Unsaturated hydrocarbons can also react with hydrogen by addition reactions producing a saturated hydrocarbon. C2H4 + H2 C2H6

38. Organic Reactions • Esterification • Reaction between an organic acid and an alcohol to produce an ester plus water. ethanoic Acid ethanol ethyl ethanoate water

39. ORGanic Reactions • Saponification • an ester reacts with an inorganic base to produce an alcohol and soap.

40. Organic Reactions • Fermentation • Six Carbon chains of sugar are broken down into carbon dioxide and two carbon fragments of alcohol. C6H12O6 2C2H5OH + 2CO2 • Polymerization • Polymers – long hydrocarbon chains made up of smaller covalently bonded chains called monomers. • Ex: proteins, starches, cellulose, synthetic plastics • Addition Polymerization – the joining of monomers of unsaturated compounds. 4C2H2 (C2H2)4 nC2H2 (C2H2)n • Condensation Polymerization – removal of water from hydroxyl groups and the joining of monomers by an ether or ester linkage.