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Quiz on Functional Groups
General Strategy For Naming Simple Organic Compounds (Bare bones summary sheets)
1. Find the highest priority group. These are listed in order of priority in the table of functional
groups.
2. Find the longest chain containing the highest priority group. You should know carbon chains of
length C1-C12 (listed in the table).
3. Number the longest chain containing the highest priority group to give the highest priority group
the lowest number possible in numbering the longest chain. For the first seven groups, the
functional group carbon will be number 1 (if it is the highest priority group) and the “1” can be
omitted, since it is understood that it has to be this way.
4. Usually the highest priority group is named as a suffix at the end of alkane, alk-#-ene or alk-#-yne.
The final e is dropped if the suffix begins with a vowel and it is retained if the suffix begins with a
consonant. A number will be present in front of the suffix name unless its position is
unambiguously clear (i.e. carboxyl groups aldehydes, nitriles, etc. always = 1, if highest in
priority). If there is a C/C pi functional group to identify (alkene or alkyne), the number in front
of its part of the name describes its position (see rule 6 below). If both a pi bond and a high
priority substituent are present, then two numbers may be necessary, one for each functionality.
5. Lower priority groups are named with their prefix names and their location numbers based on the
numbering of the parent chain (always true for substituents numbered 12 on the next page). The
lower priority substituents should be listed in alphabetical order. Some parts of prefix names
count in this regard and some don't. We will not emphasize this aspect in this course.
6. Double bonds and triple bonds are named as alk-#-ene or alk-#-yne, respectively. If both are
present, name as alk-#-en-#-yne. Multiple pi bonds (or other substituents) use the prefixes di, tri,
tetra, penta etc. with a number for each occurrence. In such cases, an "a" is added in front of the
numerical prefix for better phonetics. (alka-#,#-diene or alka-#,#,#-triyne, alka-#,#-dien-#,#diyne, etc.)
The essential functional groups to know (for our course) and their prefixes and suffixes are given in the
attached table. In this table the term “alkan-#-suffix” is a generic term for any alkane with a functional
group suffix, and it must be replaced with the correct parent stem name based on the number of carbons in
the longest chain (C1-C12 for us). If there is a double bond, the name will change to “alk-#-en-#-suffix
and if there is a triple bond, the name will change to “alk-#-yn-#-suffix.
O
2
O
1
1
4S
2Z
C
6
7
H
4
5
3
1
2
OH
2
8
1
H
3
4
2
O
(2Z,4S)-3-ethoxy-4-methyl-8-oxooct-2-en-6-ynoic acid
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Notice that no "1" is used for the carboxylic acid
group, because it has to be "1" in this structure.
Quiz on Functional Groups
Functional Group
prefix
suffix
not considered
alkanoic acid
not considered
alkanoic anhydride
(if symmetrical)
not considered
alkyl alkanoate
(R') (RCO2)
#-chlorocarbonyl
alkanoyl chloride
#-carbamoyl
alkanamide
O
1. Carboxylic acid
R
2. Anhydride
R
C
O
O
C
C
O
OH
R
O
3. Ester
R
C
O
R'
O
4. Acid halide
R
C
Cl
O
5. Amide
R
6. Nitrile
C
"R" = carbon chains
NH2
R C N
R
C
alkanenitrile
#-oxo
alkanal
#-oxo (older = #-keto)
#-alkanone
#-hydroxy
#-alkanol
#-mercapto
#-alkanethiol
#-amino
#-alkylamine / #-alkanamine
H
O
8. Ketone
R
9. Alcohol
10. Thiol
C
R'
R OH
R SH
11. Amine
R NH2
12. Ether
R O R'
12. Halogen
R X
#-alkoxy (if more than 5C's, then #-alkoxyl)
(can also use "#-oxa" prefix and
count as carbon in longest chain)
#-fluoro, #-chloro, #-bromo, #-iodo
12. Azide*
R N3
#-azido
12. Diazo*
12. Nitro*
12. Nitroso
R NO2
alkyl
branch
name
methane
ethane
propane
butane
pentane
hexane
heptane
octane
nonane
decane
undecane
dodecane
methyl
ethyl
propyl
butyl
pentyl
hexyl
heptyl
octyl
nonyl
decyl
undecyl
dodecyl
#-nitro
#-nitroso
R NO
12. Carbon branches
1
2
3
4
5
6
7
8
9
10
11
12
alkane
chain
name
always prefixes
(no suffix names)
#-diazo
R N2
#
carbons
#-cyano
O
7. Aldehyde
The part of each name
specific to the functional
group is in bold and
underlined to help you
see those features.
#-alkyl, #-(alk-#-enyl), #-(alk-#-ynyl)
R
* = formal charge is necessary in these Lewis structures and there are two reasonable resonance structures
stereoisomerism
R/S and E/Z
prefixes
parent stem C/C pi bonds
branches and
see box
above
low priority
functional groups
-ene
-yne
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
high priority suffix
see list
above
Quiz on Functional Groups
CH3CO2H
G = aldehyde
F = nitrile
CH3CN
CH3CO2CH3
CH3COCl
CH3CO2COCH3
H = ketone
CH3CHO
CH3SCH3
CH3NHCH3
CH3N(CH3)2
o
o
o
Q = alkane
P = alkyne
CH3CCH
C
H3C
C
O
H3C
CH3
H3C
H = ketone
O
O
C
C
H3C
H
H3C
C
H3C
H3C
CH3
NH2
H3C
Q = alkane
CH3
H3C
CH3
O = alkene
H
C
H2C
Br
T = diazoalkane
S = nitrosoalkane
R = nitroalkane
O
H3C
C
C
H
H3C
CH3
C
H2
H3C
H3C
N
C
H2
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
O
N
C
H2
H2C
O
SH
C
H2
H2
C
N
CH3
N
H
C
H2
P = alkyne
H3C
CH3
N = bromoalkane
H3C
S
H3C
NH2
K = thiol
O
OH
C
H2
L = sulfide / thioether M = amine (1o,2o,3o)
H3C
O
J = ether
I = alcohol
C
CH3
H3C
Cl
CH3
O
O
H3C
N
E = amide
D = ester
C
O
G = aldehyde
CH2NN
O
C
C
OH
T = diazoalkane
CH3CH2NO
C = acid chloride
O
CH2CHCH3
CH3CH2Br
S = nitrosoalkane
CH3CH2NO2
B = anhydride
O
F = nitrile
3
R = nitroalkane
CH2CHCH3
A = carboxylic acid
H3C
2
CH3CH2SH
O = alkene
N = bromoalkane
CH3CH2NH2
1
K = thiol
CH3OCH3
CH3CH2OH
L = sulfide / thioether M = amine (1o,2o,3o)
CH3CONH2
J = ether
I = alcohol
CH3COCH3
E = amide
D = ester
C = acid chloride
B = anhydride
A = carboxylic acid
N
N
CH3
Quiz on Functional Groups
Match the name and functional group with the proper structure.
A
Names
Letter
1. carboxylic acid
propanoic acid
2. anhydride
ethanoic anhydride
3. ester
ethyl propanoate
4. acid chloride
propanoyl chloride
5. amide
butanamide
6. nitrile
hexanenitrile
7. aldehyde
butanal
8. ketone
pentan-2-one
9. alcohol
hexan-3-ol
10. amine
propan-1-amine
11. ether
1-ethoxypropane
12. thiol
pentane-2-thiol
13. "halo" alkane
1-bromobutane
14. alkene
pent-2E-ene
15. alkyne
but-1-yne
16. alkane
hexane
_____
H3C
C
H2
D
O
_____
B
H2
C
H2
C
C
H2
H3C
_____
C
H2
_____
O
G
H2
C
C
H3C
C
K
_____
_____
H3C
_____
N
O
O
C
C
L
H2
C
O
H2
C
CH3
C
H3C
C
H2
H2
C
C
H2
NH2
H3C
C
H2
OH
P
O
H2
C
H3C
C
CH3
H2
C
H3C
CH
C
H2
Cl
C
H2
H
M
CH3
CH
CH3
O
_____
Br
J
H
C
C
H
H2
C
H3C
O
H3C
C
H2
H
_____
_____
H3C
H2
C
C
_____
_____
H2
C
H2
C
H3C
CH3
OH
F
NH2
I
H2
C
H3C
C
H2
C
H2
C
C
H2
C
H3C
H
_____
_____
CH3
H3C
O
H2
C
O
CH3
C
H2
C
H2
H2
C
C
_____
O
H3C
E
_____
O
C
H2
C
CH3
H2
C
C
H2
C
H2
C
N
SH
Possible Solutions:
E
O
C
H3 C
K
O
C
H3C
C
H3C
carboxylic acid
propanoic acid
D
O
C
OH
C
H2
O
O
H2
C
C
H2
H2
C
C
O
H3C
C
H2
CH
C
H2
thiol
pentane-2-thiol
I
H2
C
H3 C
CH3
alkene
pent-2E-ene
C
H2
H
CH3
C
H2
H3C
C
H2
H3C
C
H2
H3 C
alkyne
but-1-yne
"halo" alkane
1-bromobutane
A
H2
C
H3 C
C
C
H
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
H2
C
C
H2
alkane
hexane
H2
C
C
H2
CH3
C
H2
CH3
C
H2
OH
H2
C
CH3
ether
1-ethoxypropane
H2
C
CH
alcohol
hexan-3-ol
O
NH2
H2
C
H2
C
CH3
F
H2
C
NH2
C
H2
amide
butanamide
H3C
ketone
pentan-2-one
amine
propan-1-amine
SH
H2
C
C
H3 C
Cl
L
H3C
B
H2
C
H3 C
H
C
C
H
M
C
acid chloride
propanoyl chloride
C
H
H2
C
C
H2
CH3
O
aldehyde
butanal
H2
C
H3 C
G
C
N
nitrile
hexanenitrile
H3 C
O
ester
ethyl propanoate
J
H2
C
C
H2
C
O
O
N
H2
C
C
H2
CH3
anhydride
ethanoic anhydride
P
H3C
O
Br
Quiz on Functional Groups
Match the substitution patterns as primary, secondary or tertiary (alcohols, halides, amines and amides).
Point out any quarternary centers too (cannot be substituted). Identify at least two methyl, methylene,
methine (= methylidene), vinyl, allyl, phenyl and benzyl positions.
B
A
C
D
E
F
O
NH2
OH
NH2
NH2
OH
G
I
H
K
J
O
L
F
H
N
N
Br
N
H
Cl
M
O
N
OH
Q
P
O
NH2
N
N
4o
1o, methyl
A
3
allyl, 2o, methylene
B
C
allyl, 2o,
methylene
o
D
1o amine
1o alcohol
vinyl
vinyl
NH2
OH
OH
E
allyl, 3o, methine
2o, methylene
3o alcohol
G
F
O
2o, methine
4o
NH2
o
1 amide
methyl
O
Br
NH2
o
I
methine
3o, methine
1 , methyl
1 amine
4o ammonium ion
o
1o RX compound
K
2 RX compound
L
F
Cl
1o, methylene
N
H
1o, methyl
o
2 amide
M
OH
H
N
N
1o, methylene
N
H
1o, methylene
o
J
2o, methylene
1o, methylene
benzyl, methylene
3o RX compound
1o, methyl
O
2o alcohol, methine
2o amine
P
O
Q
NH2
benzyl, methyl
N
N
3o amine
3o, methine
phenyl
position
3o amide
2o, methylene
o
3o
1 amine
1o, methylene
2o, methylene
methyl
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups
Match the structures with their common names and identify any “X” substitution patterns as primary,
secondary, tertiary, vinyl, allyl, propargyl, phenyl and benzylic positions.
1. n-propyl X
A
B
D
C
E
2. isopropyl X
X
X
3. n-butyl X
X
X
4. sec-butyl X
5. isobutyl X
X
F
G
I
H
J
X
X
6. t-butyl X
X
X
7. neopentyl X
X
8. vinyl X
9. allyl X
N
M
L
K
10. propargyl X
X
X
X
11. phenyl X
X
12. benzyl X
13. neoheptyl X
14. t-hexyl X
Answers:
B
A
C
F
E
D
X
X
X
X
X
sec-butyl X
I
H
G
X
X
isobutyl X
neopentyl X
benzyl X
n-propyl X
K
J
X
vinyl X
X
X
X
t-butyl X
phenyl X
n-butyl X
M
L
X
neoheptyl X
allyl X
N
X
isopropyl X
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
X
propargyl X
t-hexyl
Quiz on Functional Groups
Name _______________________________
Match the name with a structure below. There is a correct structure and an incorrect structure for each
functional group.
Names
Letter
A
1. decanoic acid
_____
H3C
2. ethanoic anhydride
_____
3. ethyl hexanoate
_____
4. heptanoyl chloride
_____
5. pentanamide
_____
6. octanenitrile
_____
7. butanal
_____
8. nonan-4-one
_____
9. hexan-3-ol
_____
10. undecan-2-amine
_____
11. 1-propoxypropane
C
_____
13. bromomethane
_____
14. hex-1-ene
H2
C
C
H2
C
H3C
H3C
C
H2
CH
H3C
C
H2
OH
H2
C
C
H2
C
C
H2
C
H2
Cl
O
H2
C
CH3
CH3
O
H2
C
H2
C
H3C
H2
C
C
H2
C
C
H2
C
H2
H
Q
P
H3C
H2
C
C
H2
NH2
H2
C
C
C
H2
H3C
C
H2
C
O
C
H2
H3C
H2
C
C
H2
Br
N
H2
C
C
H2
C
H
O
H2
C
CH3
C
H2
CH2
C
H2
U
H2
C
H3C
C
H2
C
H3C
T
H2
C
H2
C
CH3
H
C
H2
H2
C
K
H2
C
C
H2
Br
C
M
S
C
H2
C
H2
H2
C
C
H2
C
R
H3C
C
H2
CH3
O
O
C
H2
C
H3C
NH2
SH
O
C
H2
C
O
CH3
J
H2
C
H2
C
H
L
_____
E
C
H2
H3C
O
H2
C
OH
O
C
H2
CH3
C
H2
H2
C
C
H2
H2
C
C
O
C
C
H2
G
O
C
16. octane
C
H2
H2
C
C
H2
H2
C
O
H3C
_____
C
H2
H3C
C
H2
C
H2
I
C
H2
H2
C
O
H2
C
15. hex-1-yne
H2
C
CH3
F
H3C
H3C
H3C
H2
C
O
O
_____
N
C
H2
H2
C
D
C
H3C
H2
C
H2
C
CH3
C
H2
O
H3C
O
B
H2
C
C
H2
_____
12. dodecane-3-thiol
H2
C
H2
C
CH
C
H3C
C
H2
H
NH2
V
O
H3C
C
C
H2
W
O
C
O
CH3
C
H2
X
O
H2
C
H3C
C
H2
H3C
C
C
H2
Z
H2
C
H2
C
C
H2
H3C
C
H2
H2
C
C
H2
H2
C
C
H2
H2
C
C
H2
H3C
C
H2
H2
C
C
H2
H2
C
C
H2
H2
C
C
H2
C
H2
H2
C
H3C
SH
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
H2
C
CH2
H3C
C
H
H2
C
H2
C
H3C
C
H2
H2
C
C
C
H2
C
H2
CH3
EE
DD
CH3
Y
CH3
C
H2
O
CH3
OH
H2
C
CH
H2
C
CH
NH2
H2
C
CH
BB
H3C
CC
H2
C
OH
H2
C
CH3
CH
C
H2
Cl
AA
H2
C
H2
C
C
H2
H2
C
C
H2
H2
C
C
H2
FF
CH4
C
N
H3C
C
C
H
Quiz on Functional Groups
Name _______________________________
Match the name with a structure below. There is a correct structure and an incorrect structure for each
functional group.
Names
Letter
A
1. decanoic acid
__B__
H3C
2. ethanoic anhydride
__I__
3. ethyl hexanoate
__F__
4. heptanoyl chloride
__K__
5. pentanamide
__N__
6. octanenitrile
_DD_
7. butanal
__U__
8. nonan-4-one
_BB_
9. hexan-3-ol
_AA_
10. undecan-2-amine
__Z__
11. 1-propoxypropane
C
_CC_
13. bromomethane
__S__
14. hex-1-ene
C
H2
H3C
H2
C
CH3
H2
C
H3C
C
H2
H2
C
O
C
H2
C
H2
H3C
16. octane
__A__
H2
C
H3C
C
H2
O
H2
C
H3C
C
H2
OH
H2
C
C
H2
C
C
H2
C
H2
CH
H2
C
CH3
Cl
O
H2
C
C
H2
CH3
K
M
__Q__
Br
C
C
H2
C
H3C
L
__O__
C
H2
CH3
O
C
H2
C
H3C
NH2
O
CH3
H2
C
H2
C
H2
C
H
J
CH3
C
C
H2
H3C
O
O
OH
O
H2
C
O
C
C
H2
E
G
C
C
H2
C
C
H2
H2
C
C
H2
O
H2
C
15. hex-1-yne
C
H2
H2
C
C
H2
F
H3C
C
H2
H2
C
O
O
I
H2
C
D
C
H3C
H2
C
H2
C
CH3
C
H2
O
H3C
O
B
H2
C
C
H2
__P__
12. dodecane-3-thiol
H2
C
H2
C
H2
C
H3C
H2
C
C
H2
C
C
H2
C
H2
H
SH
N
H2
C
H3C
C
H2
H2
C
H3C
C
C
H2
H2
C
C
H2
NH2
C
H2
H3C
H2
C
H2
C
C
H2
Br
N
H2
C
C
H2
C
H
O
H2
C
CH3
C
H2
CH2
C
H2
H3C
U
H2
C
H3C
C
H2
C
CH3
T
H2
C
C
H2
C
H2
H2
C
O
C
H2
H3C
C
S
H3C
H2
C
C
H
R
H2
C
Q
P
O
O
CH
C
H3C
C
H2
H
NH2
V
O
H3C
C
C
H2
W
O
C
O
CH3
C
H2
X
O
H2
C
H3C
C
H2
H3C
C
C
H2
Z
H2
C
H2
C
C
H2
H3C
C
H2
H2
C
C
H2
H2
C
C
H2
H2
C
C
H2
H3C
C
H2
H2
C
C
H2
H2
C
C
H2
H2
C
C
H2
C
H2
H2
C
H3C
SH
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
H2
C
CH2
H3C
C
H
H2
C
H2
C
H3C
C
H2
H2
C
C
C
H2
C
H2
CH3
EE
DD
CH3
Y
CH3
C
H2
O
CH3
OH
H2
C
CH
H2
C
CH
NH2
H2
C
CH
BB
H3C
CC
H2
C
OH
H2
C
CH3
CH
C
H2
Cl
AA
H2
C
H2
C
C
H2
H2
C
C
H2
H2
C
C
H2
FF
CH4
C
N
H3C
C
C
H
Quiz on Functional Groups
There are over 100 functional group patterns in organic chemistry. The following are commonly encountered functional
groups in first year organic chemistry. A specific example of each functional group with a name is give so that you can use
this as a study sheet. You will need to know all of these functional groups and how to name simple examples on the midterm.
A nomenclature quiz is possible at any time during the course. You will be allowed to use your own, self-generated
nomenclature worksheet on any of these quizzes. I would suggest making one before the next lecture, and using it on
homework sets too.
carboxylic acids
anhydrides
O
C
O
H
C
H3C
OH
O
C
C
H2
H3C
Cl
C
H2
H2
C
C
H2
O
C
C
H2
H2
C
O
C
H2
C
CH3
amines
C
H2
C
H2
H2
C
C
H2
H2
C
alkenes
C
H
H
C
C
H2
H2
C
CH3
hept-3E-ene
CH
H2
C
CH3
C
H
hexan-3-ol
H2
C C C CH3
hex-1-en-4-yne
H3C
H2
C
CH3
CH
O
CH3
CH3
2-ethyxypropane
fluoro,chloro,bromo,iodo
compounds
H3C
H2C C C CH3
pent-2-yne
nitro compounds
alkenyne
H2C
H3C
H
N
alkynes
H2
C
OH
CH
CH3
C
C
H2 H2
ethers
N-methyl-2-butanamine
octane-1-thiol
H3C
SH
H2
C
H3C
hexan-2-one
thiols
H2
C
propanenitrile
alcohols
H3C
hexanal
CH3
O
H3C
H2C C N
NH2
ketones
H2 O
H2C
C
C
C
H
C
H3C
H2 H2
C
H2
methyl propanoate
pentanamide
aldehydes
H2
C
H3C
CH3
O
C
nitriles
butanoyl chloride
H3C
O
amides
acid chlorides
H3C
O
C
ethanoic anhydride
methanoic acid
H2
C
esters
Br
C
H2
H2
C
C
H2
H2
C
C
H2
Cl
1-bromo-5-chloropentane
nitroso compounds
H3C
O
CH N
O
H3C
H3C
O
CH N
H3C
2-nitropropane
2-nitrosopropane
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups
Name ______________________________
Nomenclature #1 - Provide a name for the structures and a structure for the names.
H2
C
H3C
H3C
H3C
H2
C
C
H2
H
C
C
H
C
H2
C
O
C
C
H2
C
H2
H2
C
C
H2
C
H2
H2
C
H2
C
H2
C
H2
C
C
H2
C
H2
C
H2
O
C
H2
C
H2
C
pentanoic acid
CH3
N-ethyl-2-hexanamine
H
C
H2
O
C
C
H2
CH3
Cl
H2 H2 H2 H2 H2 H2 H2
C C C C C C C CH3
C
hex-4Z-en-1-yne
dodecanamide
ethyl pentanoate
H2 H2
C C
H3C
butane-1-thiol
3-nitroheptane
O
H2 H2 H2
C C C N
H3C
H3C
O
C
H2
H2
C
H2
C
H3C
O
C
C C N
H2
F
Br
CH
C
C
H2
H2
H2
C
H3C
C
H2
H2
C
H2
C
C
H2
O
C
H2
C
2-methoxyhexane
H2
C
CH3
H2
C
C
H2
pentan-3-ol
CH3
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups
Name ______________________________
Nomenclature #2 - Provide a name for the structures and a structure for the names.
butanoic anhydride
H3C
C
H2
octanal
H3C
H
N
C
H2
dec-3E-ene
H3C
nonanoyl chloride
H2
C
C
H2
O
C
OH
H2 H2
C
C
CH C
CH3
H
CH 2
3
H2
C
C
H2
H2
C
SH
H2 H2
H2
C
C
C
CH
H3C
C
CH3
H2
N
O O
H
C
1-nitrosobutane
H2
C C C H
HC
CH3
undec-2-yne
H3C
H2
C
C
H2
pentanenitrile
1-bromo-2-fluoroheptane
H3C
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
C
H2
H2
C
C
H2
H2
C
H2 O
C C
C C NH2
H2 H2
H2 O H2
C C C
C O
C
CH3
H2 H2
H3C
nonan-4-one
H2
C
CH3 H2
CH3
CH C
C
O C
H2 H2
H3C
OH
CH CH3
C C
H2 H2
Quiz on Functional Groups
Key
butanoic anhydride
H3C
H2
C
pentanoic acid
O
C
C
H2
O
O
C
C
H2
H2
C
H3C
CH3
octanal
C
H2
H2
C
C
H2
O
C
OH
N-ethyl-2-hexanamine
H2
H2 O
C H2C C C
C C H
H3C
C
H2 H2 H2
H3C
H
N
C
H2
H2 H2
C
C
CH C
CH3
CH H2
3
b utane-1-thiol
dec-3E-ene
H2 H H2
C C C
H3C C C C
H H2 H2
H2
C
C
H2
CH3
nonanoyl chloride
H3C
H2
C
C
H2
H2
C
SH
3-nitroheptane
H2 H2
H2
C
C
C
CH
H3C
C
CH3
H2
N
O O
H2
H2 O
H3C
C H2C C C
C
C C C Cl
H2 H2 H2 H2
1-nitrosobutane
hex-4Z-en-1-yne
H2 H2 H2 O
H3C C C C N
H
C
H2
C C C H
HC
CH3
undec-2-yne
dodecanamide
H2 H2 H2 H2 H2 H2 H2
H3C C C C C C C C C C CH3
C
H2
H2
C
C
H2
H2
C
C
H2
H2
C
H2 O
C C
C C NH2
H2 H2
ethyl pentanoate
pentanenitrile
H2 H2
H3C C C
C C N
H2
1-bromo-2-fluoroheptane
Br
H3C
H2
C
F
CH
C
H2
H2 H2
C C
C C
CH3
H2 H2
nonan-4-one
H2
H2 H2 O
C
C C C
C C C
CH3
H3C
H2 H2 H2
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
H3C
H2 O H2
C C C
C O
C
CH3
H2 H2
2-methoxyhexane
H3C
CH3 H2
CH3
CH C
C
O C
H2 H2
pentan-3-ol
H3C
OH
CH CH3
C C
H2 H2
Quiz on Functional Groups
Name ______________________________
Use the examples on the reverse side of this page to fill in the functional group with the correct carbon chain. You will need to
know all of these functional groups and how to name simple example on the midterm. A nomenclature quiz is possible at any
time during the course. You will be allowed to use your own, self-generated nomenclature worksheet on any of these quizzes.
I would suggest making one before the next lecture.
carboxylic acids
anhydrides
esters
acid chlorides
amides
nitriles
aldehydes
ketones
alcohols
thiols
amines
ethers
thioethers / sulfides
alkenes
alkynes
fluoro,chloro,bromo,iodo
compounds
nitro compounds
nitro compounds
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups
carboxylic acids
anhydrides
O
C
H
R
O
esters
O
O
O
C
C
C
R
O
R
R
amides
acid chlorides
R'
O
nitriles
O
O
C
C
H
R
R
R
N
C
N
Cl
H
aldehydes
alcohols
ketones
O
O
C
C
R
R
H
R
H
R'
amines
thiols
ethers
H
H
R
O
S
R
R'
N
R
O
H
alkynes
alkenes
thioethers / sulfides
H
R
R'
R
C
S
H
fluoro,chloro,bromo,iodo
compounds
R
C
C
C
H
nitro compounds
nitro compounds
O
O
R
Cl
N
Br
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
R
O
N
H
Quiz on Functional Groups
Information and Examples
Primary carbon chain lengths
(R = carbon chain)
Branch carbon chain lengths
(drop "-ane" and add "-yl")
1 carbon = methane
2 carbons = ethane
3 carbons = propane
4 carbons = butane
5 carbons = pentane
6 carbons = hexane
7 carbons = heptane
8 carbons = octane
9 carbons = nonane
10 carbons = decane
11 carbons = undecane
12 carbons = dodecane
1 carbon = methyl
2 carbons = ethyl
3 carbons = propyl
4 carbons = butyl
5 carbons = pentyl
6 carbons = hexyl
7 carbons = heptyl
8 carbons = octyl
9 carbons = nonyl
10 carbons = decyl
11 carbons = undecyl
12 carbons = dodecyl
Functional Groups
Prefix (when lower priority) Suffix (when higher priority)*
1. carboxylic acids
not used in our course
2. anhydrides
not used in our course
3. esters (two parts)
none for now
alkyl
4. acid chlorides
none for now
5. amides
none for now
6. nitriles
cyano7. aldehydes
oxo8. ketones
oxo9. alcohols
hydroxy10. thiols
mercapto11. amines
amino12. ethers (two parts)
alkoxy13. thioethers (two parts)
alkylthio14. alkenes
none
15.alkynes
none
16. halogen compounds fluoro-, chloro-, bromo-, iodo17. nitro compounds
nitro18. nitrosonitroso-
-oic acid
-anhydride
-oate
-oyl chloride
-amide
-nitrile
-al
-one
-ol
-thiol
-amine
none
none
-ene
-yne
none
none
none
*When a suffix starts with a vowel, drop the final "e" of the name with the correct
carbon chain length.
When a suffix starts with a consonant, retain the final "e" of the chain length name.
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups
Functional groups to memorize – random quizzes at any time during the course (draw 3 from hat)
carboxylic acids
anhydrides
O
C
R
O
H
CH2
C
O
O
H
propanoic acid
acid chlorides
C
R
ethanoic anhydride
C
O
C
C
R
CH2
propanoyl chloride
H 3C
CH2
CH2
C
C
O
N
H
propanamide
(1o amide)
CH3
methyl propanoate
N
C
R
H
R
H 3C
CH2
C
N
propanenitrile
alcohols
O
O
CH2
H
N
ketones
C
R
H 3C
C
H
O
R'
H
Cl
aldehydes
O
nitriles
O
O
H 3C
H 3C
CH3
Cl
O
C
R
R
O
amides
O
C
O
O
O
C
H3C
esters
O
C
R
O
H 3C
O
H
C
R O
R
O
propanal
H
H 3C
C
CH2
CH3
amines
thiols
CH2
CH2
OH
R'
R O
R N
S
1-propanol
ethers
H
H
R
H 3C
3-pentanone
CH2
H
H 3C
H 3C
CH2
CH2
SH
1-propanthiol
thioethers / sulfides
R'
R
H 3C
CH2
S
H 3C
CH2
CH2
NH2 1-propanamine
fluoro, chloro, bromo, iodo compds
R X
CH2
F
CH2
nitroso compounds
Br
R N
O
I
O
alkenes
H
H
C
H
alkynes
R C
C
C H
H
H
C
H 3C
nitromethane
O
3-bromo-5-chloro-7-fluoro-1-iodooctane
R
nitrosomethane
CH3
1-ethoxypropane
ethyl propyl ether
R N
R N
O
CH2
CH2
nitro compounds
X = halogen
Cl
O
R N
O
O
S
CH3
1-ethylthiopropane
ethyl propyl sulfide
CH2
C
propene
H
simple alkyl, alkenyl, alkynly chains
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
H 3C
C
C H
propyne