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Hydrocarbons

Hydrocarbons. Alkanes, alkenes and alkynes. Organic compounds. Carbon based compounds Can be bonded to other elements (H, O, N, S and halogens) Carbon makes 4 bonds , which can be single, double or triple Isomers: same molecular formula (# of each atom) but different arrangement.

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Hydrocarbons

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  1. Hydrocarbons Alkanes, alkenes and alkynes

  2. Organic compounds • Carbon based compounds • Can be bonded to other elements (H, O, N, S and halogens) • Carbon makes 4 bonds, which can be single, double or triple • Isomers: same molecular formula (# of each atom) but different arrangement

  3. Types of Hydrocarbons • Saturated: Contain the maximum number of hydrogens, single bonds between all carbons • Unsaturated: Contain 1+ double or triple bonds

  4. Types of Hydrocarbons • Aliphathic Carbons are arranged in chains • Cyclic: Carbons are arranged in rings • Aromatic: Contain a benzene ring

  5. Types of Hydrocarbons

  6. Structural Shorthand Explicit hydrogens (those required to complete carbon’s valence) are usually left off of drawings of hydrocarbons C1 C2 C3 C4 C1 C3 C4 C2 Line intersections represent carbon atoms

  7. Hydrocarbon Root Names

  8. Naming Alkanes Based off the number of C atoms in the longest chain • Count the number of C’s in the longest chain • Determine the appropriate root • Add the suffix “ane” 3 carbons 3 Carbons = Prop 3. Propane

  9. Naming Branched Alkanes Based off the number of C atoms in the longest chain • Count the number of C’s in the longest chain • Determine the appropriate root • Use the numbered C’s to give the branches a position number add “yl” suffix • Add the suffix “ane”

  10. Rules for Naming Alkanes (Nomenclature) For a branched hydrocarbon, the longest continuous chain of carbon atoms gives the root name for the hydrocarbon 1 2 3 4 4 carbon chain = butane

  11. Naming Branched Alkanes Important Rules: • Start numbering from the end that will give you the lowest number of branches • If there is more than one type of branch, name the branches in alphabetical order • If there is more than two of the same type of branch, give the branch a position number and prefixes “di”, “tri” “tetra” etc. • Put commas between numbers and hyphens between numbers and letters

  12. Rules for Naming Alkanes (Nomenclature) When alkane groups appear as substituents, they are named by dropping the -ane and adding -yl. —CH3 Methyl —CH2CH3 Ethyl —CH2CH2CH3 Propyl —CH2CH2CH2CH3 Butyl Methyl

  13. Rules for Naming Alkanes (Nomenclature) The positions of substituent groups are specified by numbering the longest chain of carbon atoms sequentially, starting at the end closest to the branching. 1 2 3 4 Methyl

  14. Rules for Naming Alkanes (Nomenclature) The location and name of each substituent are followed by the root alkane name. The substituents are listed in alphabetical order (irrespective of any prefix), and the prefixes di-, tri-, etc. are used to indicate multiple identical substituents. 1 2 3 4 Name: 2-methylbutane Methyl

  15. Nomenclature Practice Name this compound Step #1: For a branched hydrocarbon, the longest continuous chain of carbon atoms gives the root name for the hydrocarbon 1 9 carbons = nonane 2 4 3 5 6 7 8 9

  16. Nomenclature Practice Name this compound 9 carbons = nonane 1 2 4 3 5 6 CH3 = methyl 7 chlorine = chloro 8 9 Step #2: When alkane groups appear as substituents, they are named by dropping the -ane and adding -yl.

  17. Nomenclature Practice Name this compound Step #3: The positions of substituent groups are specified by numbering the longest chain of carbon atoms sequentially, starting at the end closest to the branching. 9 carbons = nonane 1 2 4 3 5 6 CH3 = methyl 7 chlorine = chloro 8 9 1 9 NOT 9 1

  18. Nomenclature Practice Name this compound 9 carbons = nonane 1 Step #4: The location and name of each substituent are followed by the root alkane name. The substituents are listed in alphabetical order (irrespective of any prefix), and the prefixes di-, tri-, etc. are used to indicate multiple identical substituents. 2 4 3 5 6 CH3 = methyl 7 chlorine = chloro 8 9 2-chloro-3,6-dimethylnonane

  19. Naming Cyclic AlkanesAdd prefix “cyclo” Cyclopropane, C3H6 Cyclobutane, C4H8 Cyclopentane, C5H10 Cyclohexane, C6H12 Cycloheptane, C7H14 Remember, explicit hydrogens are left out

  20. Naming Alkenes & Alkynes • Count the number of C’s in the longest chain containing the double/triple bond. • This is the parent chain, determine the root • Number the parent chain so that the double/triple bond has the lowest possible position number • Identify the position numbers of branches • Same rules as before • Write the branches in alphabetical order • Write the root, including a prefix that identifies the position of the double/triple bond • Add the prefix “cyclo” if its cyclic • Add the suffix “ene” if double bond or “yne” if triple bond

  21. Naming Aromatics Benzene: Cyclic 6 carbon ring of alternating single and double bonds (which gives it special properties) • Same rules • If benzene is the parent chain “benzene” suffix • If benzene is a branch group “phenyl”

  22. Cis/Trans Isomers Cis Trans

  23. Naming Halo-alkanes/alkenes/alkynes • Halogen: group 17, 7 valence shell electrons, form 1 single bond

  24. Naming Halo-alkanes/alkenes/alkynes • Same rules as a side change • Side chain name: First part of halogen with –o: • Fluoro, Chloro, Bromo, Iodo • Often Represented as R-X • R = any hydrocarbon chain • X = halogen • Ex: Longest chain is 5 carbons = pentane Only side chain is bromine = bromo Bromine at carbon 1 = 1-bromopentane

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