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Ejercicios Nomen Alcanos

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84 CHAPTER TWO Alkanes

2.17 From among the 18 constitutional isomers of C8H18, write structural formulas, and give the
IUPAC names for those that are named as derivatives of
(a) Heptane (c) Pentane
(b) Hexane (d) Butane
2.18 Write a structural formula for each of the following compounds:
(a) 6-Isopropyl-2,3-dimethylnonane (e) Cyclobutylcyclopentane
(b) 4-tert-Butyl-3-methylheptane (f) (2,2-Dimethylpropyl)cyclohexane
(c) 4-Isobutyl-1,1-dimethylcyclohexane (g) Pentacosane
(d) sec-Butylcycloheptane (h) 10-(1-methylpentyl)pentacosane
2.19 Give the IUPAC name for each of the following compounds:
(a) CH3(CH2)25CH3 (e)

(b) (CH3)2CHCH2(CH2)14CH3 (f)

(c) (CH3CH2)3CCH(CH2CH3)2 (g)

(d)

2.20 All the parts of this problem refer to the alkane having the carbon skeleton shown.

(a) What is the molecular formula of this alkane?


(b) What is its IUPAC name?
(c) How many methyl groups are present in this alkane? Methylene groups? Methine
groups?
(d) How many carbon atoms are primary? Secondary? Tertiary? Quaternary?
2.21 Give the IUPAC name for each of the following alkyl groups, and classify each one as pri-
mary, secondary, or tertiary:
(a) CH3(CH2)10CH2± (b) ±CH2CH2CHCH2CH2CH3
W
CH2CH3
Problems 85

(c) ±C(CH2CH3)3
(e) ±CH2CH2±

(d) ±CHCH2CH2CH3
(f) ±CH±
W
CH3
2.22 Pristane is an alkane that is present to the extent of about 14% in shark liver oil. Its IUPAC
name is 2,6,10,14-tetramethylpentadecane. Write its structural formula.
2.23 Hectane is the IUPAC name for the unbranched alkane that contains 100 carbon atoms.
(a) How many s bonds are there in hectane?
(b) How many alkanes have names of the type x-methylhectane?
(c) How many alkanes have names of the type 2, x-dimethylhectane?
2.24 Which of the compounds in each of the following groups are isomers?
(a) Butane, cyclobutane, isobutane, 2-methylbutane
(b) Cyclopentane, neopentane, 2,2-dimethylpentane, 2,2,3-trimethylbutane
(c) Cyclohexane, hexane, methylcyclopentane, 1,1,2-trimethylcyclopropane
(d) Ethylcyclopropane, 1,1-dimethylcyclopropane, 1-cyclopropylpropane, cyclopentane
(e) 4-Methyltetradecane, 2,3,4,5-tetramethyldecane, pentadecane, 4-cyclobutyldecane
2.25 Epichlorohydrin is the common name of an industrial chemical used as a component in
epoxy cement. The molecular formula of epichlorohydrin is C3H5ClO. Epichlorohydrin has an
epoxide functional group; it does not have a methyl group. Write a structural formula for epichloro-
hydrin.
2.26 (a) Complete the structure of the pain-relieving drug ibuprofen on the basis of the fact that
ibuprofen is a carboxylic acid that has the molecular formula C13H18O2, X is an isobutyl
group, and Y is a methyl group.

Y
W
X± ±CH±Z

(b) Mandelonitrile may be obtained from peach flowers. Derive its structure from the
template in part (a) given that X is hydrogen, Y is the functional group that character-
izes alcohols, and Z characterizes nitriles.
2.27 Isoamyl acetate is the common name of the substance most responsible for the characteris-
tic odor of bananas. Write a structural formula for isoamyl acetate, given the information that it
is an ester in which the carbonyl group bears a methyl substituent and there is a 3-methylbutyl
group attached to one of the oxygens.
2.28 n-Butyl mercaptan is the common name of a foul-smelling substance obtained from skunk
fluid. It is a thiol of the type RX, where R is an n-butyl group and X is the functional group that
characterizes a thiol. Write a structural formula for this substance.
2.29 Some of the most important organic compounds in biochemistry are the a-amino acids, rep-
resented by the general formula shown.

O
X
RCHCO2
W
1
NH3

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