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SCH 3U:
Assignment– Organic Nomenclature-ANSWERS
#1 #4 (pg 567)
a) 3-ethyl-2,4-dimethylhexane
b) 2,4,4—trimethyl-1-pentene
c) 4-ethyl-3-propyl-1-hexyne
d) 2-ethyl-3,4,5,6-tetramethyl-1-cycloheptene
#1 #5 (pg 567)
CH3-CH-CH = C-CH2-CH3
CH3
b)
CH3
CH3-C ≡ C – C - CH-CH2-CH3
CH3-CH2-CH2 CH2-CH3
CH3
c)
CH3 CH2-CH3 CH3 CH3
CH3- CH - CH – CH – C – CH2 – CH – CH – CH2 - CH3
CH3 -CH2
d)
CH3-CH2
CH2-CH2-CH3
CH3
CH = C
CH2 –CH2 - CH3
#1
#6 (pg 567)
C3H4 (require 3)
CH≡C-CH3
propyne
CH2=C=CH2
1,2-propadiene
cyclopropene
b) C5H12 (require 3)
CH3
CH3-CH2-CH2-CH2-CH3
pentane
CH3-CH-CH2-CH3
2-methylbutane
CH3
CH3-C-CH3
CH3
2,2-dimethylpropane
c) C5H10 (require 5)
CH3
CH2=C-CH2- CH3
CH3
CH3
CH2-CH3
CH= CH
CH = CH
CH2-CH3
2-methyl-1-butene
CH3 CH3
C = CH
CH3
trans-2-pentene
cis-2-pentene
cis-2-methyl-2-butene
CH2=CH-CH2-CH2-CH3
1-pentene
cyclopentane
#7 (pg 567)
a) there should be a double bond on “2” & numbered from the right side
2-methyl-2-butene
b) It is numbered incorrectly – the dble bond has to be low
3-ethyl-5,6-dimethyl-1-cyclohexene
8. a) propadienne
b) 2-methyl-1,3-butadiene
CH2=C=CH2
10. (pg 573)
d) cyclopentylcyclohexane
CH3
(pg 567)
# 9(pg 573)
c) 1,3,5-cycloheptatriene
CH2=C-CH=CH2
a) butane
b) ethane
c) 2,3,4-trimethylpentane
d) 3-ethyl-4-methylhexane
a) 2-methyl-1-propene (alkene)
b) 1-ethyl-2-methylcyclohexane (cycloalkane)
c) 3-methyl-1-pentyne (alkyne)
d) trans-3-methyl-2-pentene
(alkene)
e) 3-ethyl-3,4-dimethylhexane (alkane)
11. a) trans-2-heptene
b) cis-2-heptene
(pg 574)
12. a) = D
b) = none
c)=C
d) = A
e) = none
f) = B
13. NO! The dble bond must be the lowest number and in a cyclic compound that is #1
16 a) the “TRUE ISOMERS” of C6H14 are (a) (b) & (e)
b) (a) (c) & (d) represent the same/ identical compound
20 a)
3-ethylhexane
b) 1-butene
c)
CH2- CH3
(pg 574)
H3C CH3
CH3-CH2-CH-CH2-CH2-CH3 CH2=CH-CH2 -CH3
21.
CH3
CH3-CH2
2,3-dimethylpentane
CH2-CH2 -CH3
CH3-CH-CH-CH2-CH3
CH3-CH2
CH3-CH -CH3
methylpropane
CH2-CH2 -CH3
CH = CH
1-ethyl-3-propylcyclopentane
CH3
cis-3-methyl-3-heptene
CH2-CH2-CH2 -CH3
CHoC -CH-CH-CH2-CH2-CH2-CH3
-CH2 -CH3
CH3
3-butyl-4-methyl-1-octyne
4-ethyl-1-cyclooctene
27. Alkanes containing the fewest carbons in the main chain have the lowest BP
whereas branches increase the BP
Lowest = b) propane then d) butane then a) pentane then c) 2-methylpropane
2. Name the following organic compounds using the IUPAC system of nomenclature
a) C2H5–CCl2–CH=C(CH3)–CH2–CH3
5,5-dichloro-3-methyl-3-heptene
............................................................
CH3
C2H5
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C2H5–C(NH2)–CI–CH3
b) CH2–CC–C(NO2)–CBr–CH3
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C3H7
CH3
CH3
2-bromo-3-nitro-2,3-dimethyl-4-nonyne
...........………………………………….............
d) CHI2–CBr2–CCl2–CH3
e) CF2=CF2
3-amino-4- iodo -3,4-dimethyl
2,2-dibromo-3,3- dichloro
1,1,2,2-tetrafluoro
Hexane
1,1-diiodobutane
c)
ethene
3-cyano-1,2-dimethyl
3-chloro-2(2-chloro
4-bromo-1- cyclopropyl
cyclopentene
cyclobutyl)-1-butene
3-propyl cyclohexene
i) CH3–CH(NO2)–CH(NO2)–CH(NO2)–C2H5 j) CH3–CH – CH–CH3
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.........................................................
CH3–CH2 CH2–C2H5
2,3,4-trinitrohexane
l) H5C2 C2H5
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CF=CF
cis-3,4-difluoro
-3-hexene
m)
3,4-dimethylheptane
CH3
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CH2=C–CH=CH2
2 –methyl-1,3-butadiene
k) CH2=CH–CH=CH2
1,3-butadiene
n) NH2–(CH2)6– NH2
1,6-diaminohexane.
*o) (CH3–CHI-CHCl)2–CH–CH3
3,5-dichloro-2,6-diiodo4-methylheptane
3. Draw correct structural diagrams for the following molecules
a) 1-bromo-1-chloro-2-methylpropane
Br Cl
CH3
CH – C - CH3
d)
b) 3-ethyl-2-methylheptane
2,3,3,4-tetramethylhexane
c) 1-bromo-2-nitropentane
CH3 CH2-CH3
Br
CH3-CH-CH-CH2-CH2-CH2-CH3
CH2-CH-CH2-CH2-CH3
e) 3,3-diethyl-4-methy-5-isopropylloctane
CH3 CH3
NO2
f) cis-2,3-dimethyl-2-butene
H5C2 CH3
CH3 CH3
CH3CH – C - CHCH2CH3 CH3CH2C - CHCHCH2CH2CH3
CH3 CH3
C2H5
g) 2-methyl-1,1-dicyclopropyl-1-propene
CH(CH3)2
h) 4,4-di(2-butyl)nonane
CH3
C = CH –CH3 CH3CH2CH2 -C – (CH2)4 - CH3
3-methyl-1,4-pentadiene
C2H5
C = C
CH3 CH –CH2-CH3
j)
CH3 CH3
i) trans-3,4-dimethyl-3-hexene
CH3-CH –CH2-CH3
CH3
C = C
C2H5 CH3
k) 3-cyclopropyl-1-pentene
l) 1,2,3-trimethylcyclobutane
CH3
CH2 = CH-CH-CH =CH2 CH2 = CH-CH-CH2-CH2
CH3
CH3
m) 1,2-dicyclopropylethane
CH3
n) 2,5-dichloro-2,5-difluoro-3-hexyne
o) cis-3,4-diamino-1,3,5-heptatriene
NH2 NH2
CH2 = CH2
p)
CH3 - CFCl – C ≡ C- CFCl CH3
trans-2-pentene
q) 3,3,3-trichloropropene
CH3
CH2=CH-C = C – CH= CH-CH3
r)
2,3-dinitro-1,3-butadiene
NO2 NO2
CH= CH
CH2-CH3
CH2 = CH-CCl3
CH2 = C – C = CH2
4.a) Draw and name the 5 different isomers of hexane
n-hexane
3-methylpentane
2,3-dimethylbutane
2-methylpentane
2,2-dimethylbutane
b) Draw and name the 7 isomers of C3H4Cl2
cis-1,2-dichloropropene
trans-1,2-dichloropropene
1,1-dichloropropene
3,3-dichloropropene
1,3-dichloropropene
2,3-dichloropropene
1,1-dichlorocyclopropane
1,2-dichlorocyclopropane
5. Draw the structural diagram & name 2 different alkenes isomeric with cyclobutane
CH2=CH-CH2-CH3
CH3 CH3
CH3
CH3
CH = CH
CH = CH
CH2 = C – CH3
CH3
1-butene
cis-2-butene
trans-2-butene
2-methyl-1-propene
*6. Using the IUPAC rules name the following organic alcohols
a) CH3-CH2-CH2–OH
…1-propanol.
b) CH3-CHOH-CH3
…2-propanol
c) CH3-C(CH3)OH-CH3
…2-methyl-2-propanol
d) CH3–CHOH–CH2CH3
…2-butanol
e) CH3–C(CH3)2–CH2OH
…2,2-dimethyl-1-propanol
f) CH2OH–CH2OH
…1,2-ethandiol
*7. Using the IUPAC rules draw the following organic alcohols
a) cyclobutanol
b) 2,3-dimethyl-2-hexanol
–OH
c) 4,4-dimethyl-1,2-pentandiol
CH3 CH3
CH3
CH3 - C – CH-CH2-CH2-CH3 CH2 - CH –CH2- C –CH3
OH
OH
OH
CH3
*8. i) Write the correct name for each alcohol & ii) Which alcohol is not an isomer of all the others ? & iii) Which
alcohols are identical ?
a) CH3-C(CH3)2-CH2–OH
.... 2,2-dimethyl-1-propanol
b) C2H5-C(CH3)2–OH
......2-methyl2-butanol
c) C3H7-CHOH-CH3
.......2-pentanol
** identical
d) CH3-CH2-CH2-CH2-OH
.......1-butanol
* not an isomer
e) C2H5-CH(C2H5)-OH
.......3-pentanol
f) C4H9-CH2-OH
.......1-pentanol
*** identical
g) CH3-CHOH-CH2-CH2-CH3
.......2-pentanol
** identical
h) CH3-(CH2)3-CH2OH
.......1-pentanol
*** identical
SCH 3U:
Assignment– Organic Nomenclature-ANSWERS
#1 4 a) 3-ethyl-2,4-dimethylhexane b) 2,4,4—trimethyl-1-pentene
4 c) 4-ethyl-3-propyl-1-hexyne
d) 2-ethyl-3,4,5,6-tetramethyl-1-cycloheptene
6.a) C3H4 (require 3)
CH≡C-CH3
CH2=C=CH2
propyne
1,2-propadiene
cyclopropene
b) C5H12(require 3)
CH3
CH3-CH2-CH2-CH2-CH3
CH3
CH3-CH-CH2-CH3
pentane
CH3-C-CH3
2-methylbutane
CH3
2,2-dimethylpropane
c) C5H10(require 5)
CH3
CH2=C-CH2- CH3
CH3
CH3
CH2-CH3
CH= CH
CH = CH
CH2-CH3
2-methyl-1-butene
trans-2-pentene
CH3 CH3
C = CH
CH3
cis-2-pentene
cis-2-methyl-2-butene
CH2=CH-CH2-CH2-CH3
1-pentene
8. a) propadienne
cyclopentane
b) 2-methyl-1,3-butadiene
c) 1,3,5-cycloheptatriene
CH3
CH2=C=CH2
10.
CH2=C-CH=CH2
a) 2-methyl-1-propene (alkene)
b) 1-ethyl-2-methylcyclohexane (cycloalkane)
c) 3-methyl-1-pentyne (alkyne)
d) trans-3-methyl-2-pentene
(alkene)
e) 3-ethyl-3,4-dimethylhexane (alkane)
d) cyclopentylcyclohexane
16 a) the “TRUE ISOMERS” of C6H14 are
(a)
(b) & (e)
(a) (c) & (d) represent the same/ identical compound
21.
CH3
CH3-CH2
CH2-CH2 -CH3
CH3-CH2
CH3-CH -CH3
methylpropane
CH2-CH2 -CH3
CH = CH
1-ethyl-3-propylcyclopentane
CH3
cis-3-methyl-3-heptene
CH2-CH2-CH2 -CH3
CHoC -CH-CH-CH2-CH2-CH2-CH3
-CH2 -CH3
CH3
3-butyl-4-methyl-1-octyne
4-ethyl-1-cyclooctene
2. Name the following organic compounds using the IUPAC system of nomenclature
a) C2H5–CCl2–CH=C(CH3)–CH2–CH3
5,5-dichloro-3-methyl-3-heptene
i) CH3-CH(NO2)-CH(NO2)-CH(NO2)-C2H5
2,3,4-trinitrohexane
b) CH2–CC–C(NO2)–CBr–CH3
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C3H7
CH3
CH3
2-bromo-3-nitro-2,3-dimethyl-4-nonyne
j) CH3-CH – CH-CH3
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CH3–CH2 CH2–C2H5
k) CH2=CH–CH=CH2
3,4-dimethylheptane
1,3-butadiene
3. Draw correct structural diagrams for the following molecules
a) 1-bromo-1-chloro-2-methylpropane
Br Cl
CH3
CH – C - CH3
p) trans-2-pentene
b) 3-ethyl-2-methylheptane
CH3 CH2-CH3
Br
CH3-CH-CH-CH2-CH2-CH2-CH3
q) 3,3,3-trichloropropene
CH3
CH= CH
CH2-CH3
c) 1-bromo-2-nitropentane
NO2
CH2-CH-CH2-CH2-CH3
r) 2,3-dinitro-1,3-butadiene
NO2 NO2
CH2 = CH-CCl3
CH2 = C – C = CH3
5. Draw the structural diagram & name 2 different alkenes isomeric with cyclobutane
CH2=CH-CH2-CH3
CH3 CH3
CH3
CH3
CH = CH
CH = CH
CH2 = C – CH3
CH3
1-butene
cis-2-butene
trans-2-butene
2-methyl-1-propene
*6. Using the IUPAC rules name the following organic alcohols
a) CH3-CH2-CH2–OH
…1-propanol.
b) CH3-CHOH-CH3
…2-propanol
c) CH3-C(CH3)OH-CH3
…2-methyl-2-propanol
d) CH3–CHOH–CH2CH3
…2-butanol
e) CH3–C(CH3)2–CH2OH
…2,2-dimethyl-1-propanol
f) CH2OH–CH2OH
…1,2-ethandiol
*7. Using the IUPAC rules draw the following organic alcohols
a) cyclobutanol
–OH
b) 2,3-dimethyl-2-hexanol
c) 4,4-dimethyl-1,2-pentandiol
CH3 CH3
CH3 - C – CH-CH2-CH2-CH3
OH
CH3
CH2 - CH – CH2- C –CH3
OH
OH
CH3