SCH4U: Summary of the Rules for Naming Organic Compounds

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1 SCH4U: Summary of the Rules for Naming Organic Compounds A) Rules for Naming Saturated Hydrocarbons 1) Identify the longest unbranched carbon backbone in the molecule (parent chain). (Do not confuse bends in the chain with branches) 2) Branches on the parent chain are identified as alkyl groups (ie; methyl, ethyl, propyl...) 3) Number the carbon atoms in the parent chain beginning at the side of the closest branch group. This numbering will be used to identify the location of each alkyl group on the parent chain using the lowest possible set of numbers. 4) When a compound has multiple branches of the same alkyl group, the prefixes: di, tri, tetra etc... are used to indicate the number of each alkyl group. (ie; dimethyl) 5) When writing the name of the compound list the alkyl groups in alpha order before the parent name. Use the carbon numbers of the parent chain to indicate the location of each alkyl branch. (ie; 3-ethyl-5,5-dimethyloctane) 6) Note: Commas are used to separate numbers from other numbers in the name, while dashes are used to separate numbers and words. 7) The prefixes di, tri etc... do not count in determining the alpha order of alkyl groups. (ie: 3-ethyl-5,5-dimethyl not 5,5-dimethyl-3-ethyl) 8) If a compound yields the same set of numbers when numbered from either direction, numbering priority is given the to side with the branch that will appear first in the name. (ie; 3-ethyl-4-methylhexane not 4-ethyl-3-methylhexane) 9) Redundant numbers are usually omitted from a name. (ie; methylpropane not 2-methylpropane). B) Rules for Naming Cyclic Hydrocarbons 1) Follow the rules listed above, however, the prefix cyclo is added to the name of the cyclic hydrocarbon (ie; cyclohexane) 2) Numbering the carbons in a cyclic hydrocarbon: carbon #1 must have an alkyl group on it, then numbering continues in the direction (clockwise or counter-clockwise) that gives the smallest possible numbers to any alkyl groups. (ie; 1-ethyl-3-methylcyclohexane not 1-ethyl-5-methylcyclohexane) C) Rules for Naming Unsaturated Hydrocarbons 1) Follow the rules listed above, replacing the suffix ane with ene or yne depending on the type of multiple bonds (ie; double or triple). 2) The location of the multiple bond(s) is indicated by the carbon number immediately preceding the multiple bond. (ie; 2-hexene) 3) The location of multiple bonds takes numbering priority over the location of alkyl groups. (ie; 5-methyl-2-hexene not 2-methyl-4-hexene) 4) When possible, give the smallest possible numbers to both bonds and branches. (ie; 2-methyl-2-butene not 3-methyl-2-butene) 5) If there are more than one multiple bond in the hydrocarbon the prefixes; di, tri etc... are used to indicate the number of each multiple bond type (ie; 1,3-pentadiene) 6) Beware of geometric isomers (cis/trans) when molecular shape is indicated. Rule of Thumb Numbering priority is always given to the structural feature that is responsible for the ultimate suffix in the name of the compound. (This will apply to all functional groups) D) Review of Terms Structural Isomers: compounds having the same molecular formula but different structural formulae (ie; butane and methyl propane) Geometric Isomers: compounds having the same molecular formula and structural formula but differ in the geometric arrangement of atoms, usually around a double bond. (ie: trans-2-butene and cis-2-butene)

2 SCH4U: Organic Nomenclature: Alkanes 1) Give the correct IUPAC name for the following branched alkanes 2) Draw the structural formula for the following branched alkanes a) 2,2,3-trim ethylbutane b) 3-ethyl-2,3-dim ethylhexane c) 3-ethyl-3,5,6,7-tetram ethyl-4-propylnonane d) dim ethylpropane e) 3-ethyl-2-m ethylpentane 3) Give the correct IUPAC name for the following alicyclic alkanes 4) Draw the structural formula for the following alicyclic alkanes a) 1,1-dim ethylcyclopropane b) 4-ethyl-1,2-dim ethylcyclohexane c) 1,1,3,3-tetram ethylcyclopentane d) cycloheptane 5) Draw the structural formula and give the correct IUPAC name for six(6) structural isomers having the molecular formula: C H 7 16

3 SCH4U: Organic Nomenclature: Alkenes 1) Give the correct IUPAC name for the following alkenes 2) Draw the structural formula for the following alkenes a) 1-butene b) cyclobutene c) 4,4-dim ethyl-2-pentene d) 5-ethyl-4-propyl-2-heptene e) 3,4-dim ethyl-2,4,6-octatriene f) 4-ethyl-5-isopropyl-1,2-dim ethylcyclohexene 3) Draw the structural formula, or give the IUPAC name of the following geometric isomers a) trans-2-hexene b) cis-2-pentene 4) Briefly, explain the cause of cis/trans isomerism in the alkenes and why it doesn t occur with the alkanes or alkynes. 5) Draw the structural formula and give the IUPAC name of seven (7) structural isomers having the molecular formula: C H 5 10

4 SCH4U: Organic Nomenclature: Alkynes 2) Give the correct IUPAC name for the following alkynes 2) Draw the structural formula for the following alkynes a) propyne b) 4,4,5-trimethyl-2-hexyne c) 3-ethyl-3-m ethyl-1-pentyne d) 6-ethyl-2,3-dim ethyl-6-propyl-4-nonyne e) 3,4-diethyl-3,5,7-trim ethyl-1-decyne 3) i) Describe the bonding in the following m olecules in term of the orbital hybridization, the orbital overlap and type of bond (sigm a/pi).used by the carbon atoms. ii) W hat is the expected bond angle around the carbon atoms in the following hydrocarbons. 4) Based on your understanding of the nature of the bonds between the atoms in alkanes, alkenes and alkynes, predict the relative chemical reactivity of these fam ilies of hydrocarbons.

5 SCH4U: Aromatic Hydrocarbons Aromatics form a special group of cyclic organic compounds the simplest of which is benzene (C 6H 6). Most aromatic compounds contain one or more benzene molecules. Various depictions of the Benzene ring 2 Benzene is a resonance structure. Each carbon in the ring is using sp hybridization, allowing the unhybridized p orbitals of each carbon to form one large doughnut shaped ring of delocalized pi electrons above and below the plane of the molecule. As a result, the benzene ring does not contain any true double bonds, each bond in the ring is equal in length and strength. The delocalized nature of these pi electrons provides the benzene m olecule with unexpected stability. The benzene ring tends to rem ain intact during chem ical reactions, behaving m ore like an alkane than an alkene. Nomenclature of Aromatic Compounds W hen the benzene ring is attached to a carbon chain of 5 carbon atoms in length or less, the benzene is considered the parent hydrocarbon and the carbon chain is an alkyl branch. W hen the benzene ring is attached to a chain of 6 or more carbon atoms, or if there is a feature to the chain that gives it priority over the benzene (ie; multiple bond, functional group) then the benzene is considered a branch on this chain and is called a phenyl group.

6 -2- Special Nomenclature for Benzene Compounds substitution groups on carbons 1 and 4 = 1,4-substitution = para substitution or p substitution groups on carbons 1 and 3 = 1,3-substitution = meta substitution or m substitution groups on carbons 1 and 2 = 1,2-substitution = ortho substitution or o Reactions involving Benzene The lack of true localized double bonds in the benzene ring means that it does not undergo addition reactions typical of alkenes. Benzene will undergo substitution reactions, like the alkanes, in which one of its hydrogens will be replaced by an atom of another element. Com plete the following reactions and nam e the organic product(s):

7 SCH4U - Naming Aromatic Compounds Name or draw the structural formula for the following aromatic compounds: para-dichlorobenzene ortho-diethylbenzene 2-phenyl-2-pentene 3-m ethyl-4-phenyl-1-hexyne 1,2,3-trim ethylbenzene 2-phenylpropene

8 SCH4U: Hydrocarbon Nomenclature Review Draw the structural formula or give the correct IUPAC name for the following hydrocarbons:

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