NOMENCLATURE

ORGANNICu
J-methyloctane. Explain
I Write
Ihe
CH,-ÇH-CH-CH,-CH,-CH,
CH-CH-CH,-CH,-ÇH-CH, (c) (a) | CH,-CH-CH-CH,
2,3-dimethylbutane(a) I following
(a) Name the
longest why formulas
2-ethylheptane CH,
continuous CH, CH, for
CH, (a) compounds:
2-methyl-3-ethylhexane
chain is
not
would (b) (b)
a
standard and AND
include C--CH,CH, CH,
(c)
, CH, CH, CLASSIFICATION
H, 3 2,2-dimethylbutane CH, CH,
thIUPAC
e
ethyl (b)
5 (b)
name. 2,2-dimethylhexane
group,
CH,-C-CH,-CH,-CH,-CH,
6

7
and CH, CH,
8 (c)
compound
wouldthe Molecules
Organic
CH,-CH,-C-CH,
(c)
2,3,6-trimethylheptane
CH, CH,
havethe
CHAPTER 9
standard
name
 9.7 compound:
Gve thc svstematic name of the following
CH,CH,CHCH,CH,CH,CH, 9.
CH-CH,
CH,
I 2-Methyl-3-ethylheptane
9.8
Which of the following is(are) called methyl chloride? (a) CH,CI (6) CH,Cl, (c) CHCI, (d) CCl, (e)
your choice.

(a) The methyl group is CH,-. It results from the removal of one hydrogen atom from methane
Expk:
9.9
Give the systematic name and formula for each of the
(c) acetone (d) acetaldehyde (e) acetic acid (f) following compounds: (@) phenyl ethyl ketone (h at.3
formaldehyde
(a) 1-Phenyl-1-propanone
(b) ethene
CH,=CH,
(C) propanone
(e) ethanoic acid CH,COCH, (d) ethanal CH,CHO
CH,CO,H ) methanal HCHO
9.10
What class of compounds is
formulas for three compoundsrepresented by the
which correspondtype formula
to this type ROR? Using CH, and C&H, as the
Ethers.
they may beCH,0CH,,
formula. radicals, M:
CH,0C,Hs,
different, not that they mustC,H,0CçH,. (The fact that the
be
diferent.) radicals are denoted R and R means
 ANIC MOLECULES 0 133
Name the
thefollowing compounds:
911
(a) CH;--CH,--CH-CH,-CH (b) HO-CH,-CH,-CH-CH,
CH, CH,
OH
i HO-CH-CH, CH,CH, (d)
CH,
CH,=CH-CH,-CH-CH,
CH3
CH,
(e) CH;-CH=CH-CH,-CH, G) CH,CH,CHCH,CH,
ÇH,
C1
I(a) 2-Ethyl-1-butanol (b) 3-methyl-1-butanol (c) 3-hexanol
(d) 4-methyl-1-pentene (e) 2-pentene ) 3-(chloromethylpentane
9.12 Name the following compounds:
(a) CH,CCH,CH,CI (b) CH,(CH,),C0,H () CH,CH,CHCH,CH,CH,
CHO
CH,
(b) octanoic acid (c) 2-ethyl-1-pentanal
I(a) 4-Chloro-2-methyl-1-butene
9.13 why the name butanol is not specific, whereas the name butanone represents one specific compound.
(a) Explain
(b) Is the name pentanone specinc?
cannot have the carbonyl
mnay haye the OH group on the first or second carbon atom. Butanone 2-pentanone or
(4) Butanol functional group). (b) Pentanone could refer to
an aldehyde
80up on the end (where it would be
lo 3-pentanone, so the name is not specilic.
914 CHCH=CH, (b) (C,H),0 (c) (C,H),NH
 Name the following
i) CH,CH,CONHCH,compounds:
(e)
(a)
CH,=CH-CH=CH--CH=CH, (b) (C,H,),0 (e) (CzHs)N
(C,H,),NH$CI
(a) 1.3,5-hexatriene (b) diphenyl eth (c) diethyl amine
(d) methyl propanamide (e) diethylammonium chloride

5 Write formulas for (a) ethylamine (b) propionaldehyde (c)

)bromobenzene (9) acetylene (h) phenylacetylene butanone (d) ethyl propionate (e) butyi formate
| (a) CH,CH,NH, (b) CH,CH,CHO (c) CH,COCH,CH,
(d) CH,CH,CO,CH,CH, (e) HCO,CH,CH,CH,CH, ) C,H,Br
(g) HCECH (h) CçH,C=CH

916 Write formulas for (a) 2-butene (b) methyl ethyl ether (c) propanal (d) 2-propanol (e) 2,4-pentandione
(acetylacetone)
I (a) CH,CH=CHCH, (b) CH,OCH,CH, (c) CH,CH,CHO
(d) CH,CHOHCH, (e) CH,cOCH,COCH,

917 Write a structural formula for each of the following:

(a) 4-ethylheptane (b) 4-propylheptane (c) 4{1-methylethyl)heptane

(a) CH,CH,CH,ÇHCH,CH,CH, (b) CH,CH,CH,CHCH,CH,CH,

CH, CH,
CH,
CH,
H,
 +(CH,), NH CH,C;H, (c)
(CH,),N
CH,CH,OH (b) CH,
9.20
(6) HCKag) +
following
(a)
compounds:CH,CO,H
Name cach of the)CH,CHOHCH, (9)
(h) HOCH, (i) C,H,0H CH,CU)OCH,CH,C00
(c) CH,CHO
(k) CH,CHOCH,CH, (c) acetone (4) dimethyl ether
(b) toluene (9) aceticacid (h) ethyl alcohol
(a) Ethvl alcohol
(e) acetaldehvde
) 2-propanol (k) 2-chlorobutane
C) methyl acetate
() phenol
butyl alcohol (b) propyl phenyl ether (c) ethyl
compounds: (a)
9.21 Write formulas for the following
(d) diphenylamine
(b) CH,CH,CH,0C,H,
I(e) CH,CH,CH,CH,OH (d) (CçH), NH
CH,CO,C,H,)
(c) CH,COC,H, (often written

9.22 Classify the following molecules according to functional group:

(a) CH,CH,CH,0CH, (6) H,CCH, (c) CH,-C-CH,CH,
H,C CHOH
/
H,C-CH,
(d) CH,=CHCH,CHs (e) H,C-CH, ) H,C-CH,
H,C H,C C=0

(9) CH,=CHCH
H,C-CH, H,C-CH,
CH,
I Molecules (a) and (e) have the
(c) and (f) are ketones because they ROR' type formula and are ethers: (b), having ROH.isan
contain the C-C-Cgroup: (d) is an alkene which also Contains

group, and (g) is a diene, with two

double bonds connecting carbon
9.23 atoms.
 The carbon atoms of the benzene ring may be numbered for
25 Loins of carbon atoms are numbered. Again, the smallest set identification of substituent groups, just as continuous
of numbers designating the substituents is the pre
ferred set. Draw structures for each of the following:
(a) 1,3-dichlorobenzene (b) 2,4,6-trinitrotoluene (c) 1,4-diethylbenzene
CI (b) CH, (c) CH,CH,
O,N, NO,

NO, CH,CH
9.26 Write the formula for 1-phenyl-1-butanone. Explain why the designation "1-butanone" is somewhat unusual.
The carbonyl group positioned on an end (number 1)
-C-CH,CH,CH, carbon atom usually isa part of an aldehyde group.

9.27 In the following representation of a hydrocarbon molecule, designate the primary, secondary, tertiary, and quaternary
carbon atoms:
H H, H
H,C-c e C
-ÇH,
H-C-C-H
|h
HH
tertiary; and d is quaternary.
Oms a, b, and f are primary; c, g, and h are secondary; e is
 (a) Classify each of the following compounds as an alkane, alkene, alcohol, ether, ester, acid. amine, amide.
9.30
or ketone.
H,C-CH, CH,CONH,
CH,CH,OCH, CH,CH,CO,H
H,C C=0 CH,C0,CH,
H,C-CH,
(b) Name the comnpounds in (a).
(b) methyl ethyl ether, propanoic acid, cyclohexanone,
I (a) Ether, acid, ketone, amide, ester
methvl acetate

9.2 STRUCTURAL ISOMERISM

9.31 Which of the following formulas represent different molecules?

H (c) H H H H H
(a)
HT H
H H H CH H-C-C-C-C--C-H

H- --C-C- -H H C H HH H
H H H H H
HIH
H

(b) HH ,H (d) H H H H H

H H
H-C-C-CC-CH
H-C -C-H H HC H H
H C HH
H
H.H
H H
H
H
SeCond
ei"
I(o), (b), (c) are formulas of the
same compound. Each has a a branch at the
atom from one end. (d)represents a different molecule. since five-carbon chain with
the branch is on the th1rd cal
 3

Draw structures of all

all
isomers of C,H,CI. CH,
CH,=CHCH,CI C1 H CI
CH, H
H,C-CH,
H CH, H H H CH,
H Ci
Drw formulas for all structural isomers of
C,H,I,.
H H H H H HH H H HH H
I-C-C -C-H
H HH
I-C-C----H I-C-C-C-C-H
H I H H HH HI H
H H H H HI H H H H H H

I-C-C-C-C-I H-C-C-C-C-H H-C-C-C-C-H

H
HHH H H HI0H
H H H 0 I 0H
H H H H H H HI H
I-C-C-C-I I-C-C-C-H I-C-C-C-H

H H H H H
C
HH H H HH
H H
H

How many structural isomers are possible for C,H,CI,?

Two--1,1-dichloroethane and 1,2-dichloroethane
Draw the carbon skeleton and any chlorine atoms for all structural isomers of the following molecules. You need
not bother drawing the hydrogen atoms, but see that the correct number are present for each isomer. (a) CyHiz
(6) C,H,CI (c) C,H;Cl, (d) C,H,,CI (e) C,H14 ) C,H;6
I(e) C-C-C--C-C C-C-C-C C
C-C-C

(b) C-C-C-CI C-C-C

C-C-C CI
(c) C---C-C Ci
CI C-C-C
CI CI --C CI
Cl
CI
(d) CCCC-C C-C-C-C-C C--C-C-C--C C--C-C -C--CI
CI C
CI

C--C--C-C CI C--C-C--C
CI C-C--C---C
C- -C-C CI C
C

(e) C-C-C-C-C-C C-C-C-C-C C

C-C-C-C-C
I
C-C--C-C

C-C-C-C

f) C-C-C-C-CC-C C-C-C-C-C-C C-C-C-C--C-C

C C

C C-C-C-C--C C-C-C-C-C

C-C-C-CC C

C
C-C -C-c
C--C-C-C-C C-C-C-C