Alkane Nomenclature 3-1 The structure that corresponds with each name is drawn below. (a) sec-butylcyclohexane (b) 2,2,7-trimethyloctane (c) 3-ethyl-2,4,5-trimethylhexane (d) 1-cyclopropylbutane (e) 3-ethyl-2,5-dimethyl-4-propylheptane (f) 1-tert-butyl-4-iodocyclohexane (g) trans-1,4-diisopropylcyclohexane (h) 3-bromo-1-cyclopropyl-2-methylbutane (i) Z-1,2-dichloro-1-methylcyclopentane (j) 1-chloro-3-ethyl-3-methylhexane (k) Norbornane (Bicyclo[2.2.1]heptane) (l) 1-[2-(bromomethyl)cyclopropyl]-4-tert-butylcyclohexane 3-2 Give the IUPAC names of the following alkanes. (a) 5-ethyl-2,6-dimethyloctane (b) 3,4,7-trimethyl-6-(1-methylethyl)nonane (c) 4-(1-methylpropyl)-2,3-dimethyloctane (d) 1,3-dimethyl-2-(1-methylethyl)cyclobutane (e) 1- tert -butyl-4-ethyl-2-methylcyclopentane (f) trans -1,3-diethylcyclohexane (g) cis -1,4-di(1-methylethyl)cyclononane (h) 3-methylhexane 3-3 The following names are incorrect or incomplete, but they represent the real structures. Draw each structures and name it correctly. (a) (b) (c) (d) (e) (f) Alkyl Halide Nomenclature 3-4 a) b) c) d) e) 3-5 a) 3-chloropentane b) 1-chloro-3-methylcyclohexane c) 5-chloro-2,2-dimethylhexane d) (1R,2R)-1-bromo-2-methylcyclohexane 3-6 a) Secondary b) Primary c) Tertiary d) Tertiary Alkene Nomenclature 3-7 3-8 3-9 a) Z b) Neither c) E 3-10 Alkyne Nomenclature 3-11 a) b) c) d) e) f) 3-12 a) 1-chloropent-3-yne b) 2,2-dimethyl-6-methyl-hex-4-yne c) cyclohexylhept-1-yne d) 4-bromo-2-chloro-3-methylnon-7-yne Alcohol and Phenol Nomenclature 3-13 a) Primary b) Secondary c) Tertiary d) Secondary 3-14 3-15 3-16 Ethers 3-17 (g) oxydicyclopentane (h) 2-phenyloxirane (i) 1-cyclohexylethane-1-thiol 3-18 (a) (b) (c) 3-19 (a) diisopropylsulfide (b) 1,3-dimethoxybenzene (c) 2-Methyltetrahydro- 2H-pyran (d) methyl 3-sulfanylbenzoate (e) methyl(phenyl)sulfide Benzene and its Derivatives 3-20 A – meta; B – para; C – ortho 3-21 1,3-Dibromobenzene 1-phenyl-4-methylhexane 1,4-Dichloro-2,5-dimethylbenzene 2-methyl-1,3,5-trinitrobenzene. (Also known as trinitrotoluene, or TNT) 13-22 3-23 3-24 3-25 In order of priority: Benzoyl bromide > Amino > Nitro Aldehydes and Ketones 3-26 Amines 3-27 Carboxylic Acids 3-28 Carboxylic Acid Derivatives 3-29 3-methylpentanoyl chloride 2- cyclopentylacetamide propyl 2-methylpropanoate cyclohexylbutanoate tert-butyl cyclopentanecarboxylate 1-methylbutylcyclopentane carboxylate N-methyl-3-butenamide (S)-2-hydroxypropanoyl phosphate propyl 2,3-dimethyl-2-butenethioate