3.16: Solutions to Additional Exercises
- Page ID
- 122579
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-
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