nomen_1st_day_quiz_key_2.pdf
16
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 C 1 -C 12 (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 (C 1 -C 12 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 OH O 1 2 3 4 5 6 7 8 O H C 1 2 3 4 4S 1 1 2 2 2Z (2Z,4S)-3-ethoxy-4-methyl-8-oxooct-2-en-6-ynoic acid Notice that no "1" is used for the carboxylic acid group, because it has to be "1" in this structure. H Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
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Transcript of nomen_1st_day_quiz_key_2.pdf
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
OH
O
12
34
56
78
O
H
C
12
3 4
4S1
12
2
2Z
(2Z,4S)-3-ethoxy-4-methyl-8-oxooct-2-en-6-ynoic acidNotice that no "1" is used for the carboxylic acid group, because it has to be "1" in this structure.
H
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups Functional Group
1. Carboxylic acid
2. Anhydride
3. Ester
4. Acid halide
5. Amide
6. Nitrile
7. Aldehyde
8. Ketone
9. Alcohol
10. Thiol
11. Amine
12. Ether
12. Halogen
12. Azide*
12. Diazo*
12. Nitro*
12. Nitroso
12. Carbon branches
prefix
not considered
not considered
not considered
#-chlorocarbonyl
#-carbamoyl
#-cyano
#-oxo
#-oxo (older = #-keto)
#-hydroxy
#-mercapto
#-amino
#-alkoxy (if more than 5C's, then #-alkoxyl) (can also use "#-oxa" prefix and count as carbon in longest chain)#-fluoro, #-chloro, #-bromo, #-iodo
#-azido
#-diazo
#-nitro
#-nitroso
#-alkyl, #-(alk-#-enyl), #-(alk-#-ynyl)
suffix
alkanoic acid
alkanoic anhydride(if symmetrical)
alkyl alkanoate (R') (RCO2)
alkanoyl chloride
alkane alkyl # chain branchcarbons name name
1 methane methyl 2 ethane ethyl 3 propane propyl 4 butane butyl 5 pentane pentyl 6 hexane hexyl 7 heptane heptyl 8 octane octyl 9 nonane nonyl 10 decane decyl 11 undecane undecyl 12 dodecane dodecyl
* = formal charge is necessary in these Lewis structures and there are two reasonable resonance structures
stereoisomerism prefixes parent stem C/C pi bonds high priority suffix
alkanamide
alkanenitrile
alkanal
#-alkanone
#-alkanol
#-alkanethiol
#-alkylamine / #-alkanamine
"R" = carbon chains
R/S and E/Z branches andlow priorityfunctional groups
see box above
see list above
-ene-yne
CR
O
OH
CR
O
OCO
R
CR
O
OR'
CR
O
Cl
CR
O
NH2
CR N
CR
O
H
CR
O
R'
OHR
OR
SHR
NH2R
XR
N3R
N2R
NO2R
NOR
R'
R
always prefixes(no suffix names)
The part of each name specific to the functional group is in bold and underlined to help you see those features.
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups
CH3CN
A = carboxylic acid B = anhydride C = acid chloride D = ester E = amide
F = nitrile G = aldehyde H = ketone I = alcohol J = ether K = thiol
L = sulfide / thioether M = amine (1o,2o,3o) N = bromoalkane O = alkene
P = alkyne Q = alkane R = nitroalkane S = nitrosoalkane T = diazoalkane
CH3CO2H CH3CO2COCH3 CH3COCl CH3CO2CH3 CH3CONH2
CH3CHO CH3COCH3 CH3CH2OH CH3OCH3 CH3CH2SH
CH3SCH3 CH3CH2NH2 CH3NHCH3 CH3N(CH3)2 CH3CH2Br CH2CHCH3
CH3CCH CH2CHCH3 CH3CH2NO2 CH3CH2NO CH2NN
1o 2o 3o
H3CCH2
CH3
H3CC
O
OH H3CC
OCH3
O
H3CC
OC
CH3
O O
H3CC
Cl
O
H3CC
NH2
O
H3C C
H3CC
O
H3CC
CH3
O
H3CCH2
OHH3C
OCH3
H3C
H2C
Br H2C
HC
H3C C C H
A = carboxylic acid B = anhydride C = acid chloride D = ester E = amide
F = nitrile G = aldehyde H = ketone I = alcohol J = ether K = thiol
L = sulfide / thioether M = amine (1o,2o,3o) N = bromoalkane O = alkene
CH3
P = alkyne
N
H
Q = alkane R = nitroalkane S = nitrosoalkane T = diazoalkane
H3CCH2
SH
H3CS
CH3
H3CCH2
NH2 H3CNH
CH3
H3CN
CH3
CH3
H3CCH2
NH3C
CH2
N
O
O
O
NH2C N
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups
Match the name and functional group with the proper structure. 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
H2C
CH2
H2C
CH2
CH3 H3CCH2
C
O
OH
CH2
CO
H2C
CH3
O
H3CC
OC
CH3
O O
H3CCH2
CCl
O
H3C
H2C
CH2
CNH2
O
H3CCH2
H2C
CH2
H2C
C
H3C
H2C
CH2
C
O
H3CC
CH2
O
H2C
CH3
H3C
H2C
CH
H2C
CH2
CH3
OH
H2C
CH2
NH2
H2C
CH2
OCH2
CH3
H3CCH2
H2C
CHCH3
SH
H3C
H2C
CH2
H2C
Br
H3C
H2C
CH
HC
H3C
H2C
CC
H
A B C
D E F
G H I J
K L M
N O
H3C
H3C
H3C
CH3
P
H
N
Possible Solutions:
H3C
H2C
CH2
H2C
CH2
CH3
H3CCH2
C
O
OH CH2
CO
H2C
CH3
O
H3CC
OC
CH3
O O
H3CCH2
CCl
O
H3C
H2C
CH2
CNH2
O
H3CCH2
H2C
CH2
H2C
C H3C
H2C
CH2
C
O
H3CC
CH2
O
H2C
CH3
H3C
H2C
CH
H2C
CH2
CH3
OH
H2C
CH2
NH2H2C
CH2
OCH2
CH3H3C
CH2
H2C
CHCH3
SH
H3C
H2C
CH2
H2C
Br
H3C
H2C
CH
HC
H3C
H2C
CC
H
A
B
C D
E
F
G
HI
J
K
L
M
N
O
H3C
H3C
H3C
CH3
P
carboxylic acidpropanoic acid
anhydrideethanoic anhydride
esterethyl propanoate
amidebutanamide
"halo" alkane1-bromobutane
ketonepentan-2-one
alkynebut-1-yne
alkenepent-2E-ene
acid chloridepropanoyl chloride
alcoholhexan-3-ol
aminepropan-1-amine
thiolpentane-2-thiol
alkanehexane
nitrilehexanenitrile
aldehyde butanal
ether1-ethoxypropane
NH
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
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.
OH
OH
OH
NH2
NH2NH2
Br
Cl
F
N
NH2
O
NH
O
N
O
HN
N
F
G H I J K L
M N P
EA B C D
O Q
OH
OH
OH
NH2
NH2
NH2
Br
Cl
F
N
NH2
O
NH
O
N
O
HN
N
F G H I
J K L M
N P
E
A B C D
O Q
1o, methyl
3o
2o, methylene
allyl, 2o, methylene
vinyl
4o
allyl, 3o, methine3o alcohol 1o, methylene
1o alcohol1o amine
1o amide 1o amine 1o RX compound
1o, methylene
4o
2o RX compound
2o, methine
3o, methine
1o, methyl 2o amide
4o ammonium ion
1o, methylene 3o RX compound 2o amine
1o, methylene
2o alcohol, methine
benzyl, methylene
3o, methine
1o, methyl
phenyl position
3o amide 1o amine3o amine
3o
2o, methylene
benzyl, methyl
2o, methylene
methyl
1o, methylene
1o, methylmethyl
methine2o, methylene
vinyl
allyl, 2o, methylene
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.
X
X
X
X
XX
X
XX
X
1. n-propyl X
2. isopropyl X
3. n-butyl X
4. sec-butyl X
5. isobutyl X
6. t-butyl X
7. neopentyl X
8. vinyl X
9. allyl X
10. propargyl X
11. phenyl X
12. benzyl X
13. neoheptyl X
14. t-hexyl X
X
X
A B C D E
F G H I J
K M
X
L N
X
Answers:
X
X
X
X
XX
XX
X
X
X
X
A B C D E F
G H I J
NM
sec-butyl X
phenyl X
neopentyl X isobutyl X n-propyl X vinyl X
n-butyl X
isopropyl X
benzyl X
t-butyl X allyl X
propargyl X
K
X
L
X
neoheptyl X
t-hexyl
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
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
1. decanoic acid _____
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 _____
12. dodecane-3-thiol _____
13. bromomethane _____
14. hex-1-ene _____
15. hex-1-yne _____
16. octane _____
H3C
H2C
CH2
H2C
CH2
H2C
CH2
CH3
H3C
H2C
CH2
H2C
CH2
H2C
CH2
H2C
CH2
C
O
OH
H3C
H2C
CH2
C
O
OH
H3C
H2C
CH2
H2C
CH2
CO
H2C
CH3
O
H3CC
O
H2C
CH2
O
CH3
CH2
CO
CCH2
O
CH3
O
H3CC
OC
CH3
O O
H3C
CH2
H2C
CH2
H2C
CH2
CCl
O
H3C
H3CCH2
H2C
CH2
CCl
O
H3CCH2
H2C
CH2
CNH2
O
CH2
H2C
CH2
H2C
CH2
CNH2
O
H3C
CH2
H2C
CH2
H2C
CH2
H2C
CH3C
N
H3CCH2
H2C
CH2
H2C
CN
H3C
H2C
CH2
CH
O
CH2
H2C
CH2
H2C
CH2
CH
O
H2C
H3C
H3C
H2C
CH2
H2C
CH2
CCH2
O
H2C
CH3
H3CC
CH2
O
H2C
CH3
H3C
H2C
CH2
H2C
CH2
H2C
CH
H2C
CH2
H3C
H2C
CH
H2C
CH2
CH3
CH3
OH
OH
CH2
H2C
CH2
H2C
CH2
H2C
CHCH3
NH2
H2C
CH2
H3C
CH2
H2C
CH2
H2C
CH2
H2C
CHCH3H3C
H2C
CH2
OCH2
H2C
CH3H3C
H3CCH2
OCH2
CH3
CH2
H2C
CH2
H2C
CH2
H2C
CH
H2C
SH
H2C
CH2
H3CCH3
H3C
H2C
CH2
H2C
CH
H2C
SH
CH3
BrH3C
H3C
H2C
CH2
H2C
Br
H2C
CH2
H2C
CH
CH2
H3C
H3C
H2C
CH2
H2C
CC
H
NH2
A B
C D E
F G H
I J K
L M
N O P Q
R S T U
V W X
Z BB
CC EEDDFF
CH3C
CH4
C H
H3C
H2C
CH
CH2
Y
AA
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
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
1. decanoic acid __B__
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 __P__
12. dodecane-3-thiol _CC_
13. bromomethane __S__
14. hex-1-ene __Q__
15. hex-1-yne __O__
16. octane __A__
H3C
H2C
CH2
H2C
CH2
H2C
CH2
CH3
H3C
H2C
CH2
H2C
CH2
H2C
CH2
H2C
CH2
C
O
OH
H3C
H2C
CH2
C
O
OH
H3C
H2C
CH2
H2C
CH2
CO
H2C
CH3
O
H3CC
O
H2C
CH2
O
CH3
CH2
CO
CCH2
O
CH3
O
H3CC
OC
CH3
O O
H3C
CH2
H2C
CH2
H2C
CH2
CCl
O
H3C
H3CCH2
H2C
CH2
CCl
O
H3CCH2
H2C
CH2
CNH2
O
CH2
H2C
CH2
H2C
CH2
CNH2
O
H3C
CH2
H2C
CH2
H2C
CH2
H2C
CH3C
N
H3CCH2
H2C
CH2
H2C
CN
H3C
H2C
CH2
CH
O
CH2
H2C
CH2
H2C
CH2
CH
O
H2C
H3C
H3C
H2C
CH2
H2C
CH2
CCH2
O
H2C
CH3
H3CC
CH2
O
H2C
CH3
H3C
H2C
CH2
H2C
CH2
H2C
CH
H2C
CH2
H3C
H2C
CH
H2C
CH2
CH3
CH3
OH
OH
CH2
H2C
CH2
H2C
CH2
H2C
CHCH3
NH2
H2C
CH2
H3C
CH2
H2C
CH2
H2C
CH2
H2C
CHCH3H3C
H2C
CH2
OCH2
H2C
CH3H3C
H3CCH2
OCH2
CH3
CH2
H2C
CH2
H2C
CH2
H2C
CH
H2C
SH
H2C
CH2
H3CCH3
H3C
H2C
CH2
H2C
CH
H2C
SH
CH3
BrH3C
H3C
H2C
CH2
H2C
Br
H2C
CH2
H2C
CH
CH2
H3C
H3C
H2C
CH2
H2C
CC
H
NH2
A B
C D E
F G H
I J K
L M
N O P Q
R S T U
V W X
Z BB
CC EEDDFF
CH3C
CH4
C H
H3C
H2C
CH
CH2
Y
AA
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
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 esters
acid chlorides amides nitriles
aldehydes ketones alcohols
thiols amines ethers
alkenyne
fluoro,chloro,bromo,iodo compounds
nitro compounds nitroso compounds
alkenes alkynes
CH
O
OH
methanoic acid ethanoic anhydride
CH3C
O
OCO
CH3C
CH2
O
OH3C CH3
methyl propanoate
CCH2
O
Cl
H2C
H3C
CCH2
O
CH3
H2C
CH2
H3C
CCH2
O
NH2
H2C
CH2
H3C
CCH2
O
H
H2C
CH2
H2CH3C
C CH2CH3C
C NH2CH3C
butanoyl chloride pentanamide propanenitrile
hexanal hexan-2-one hexan-3-ol
octane-1-thiol N-methyl-2-butanamine 2-ethyxypropane
hept-3E-ene pent-2-yne 1-bromo-5-chloropentane
2-nitropropane
CH3
H3C
H2C
CH2
CHCH2
CH3
OH
H3C
H2C
OCH
CH3
CH3
H3CHN
CH
H2C
CH3
CH3
H3C
H2C
CH2
H2C
CH2
H2C
CH2
H2C
SH
H3C
H2C
CH
HC
CH2
H2C
CH3 CH2
H2C
CH2
H2C
CH2
ClBr
NCHO
O
H3C
H3C
2-nitrosopropanehex-1-en-4-yne
NCHOH3C
H3CC C CH3
H2CC
HH2C
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.
pentanoic acidC
CH2
O
OCO
CH2
ethyl pentanoate
CCH2
O
CH2
H2C
CH2
H2C
CCH2
O
H
H2C
CH2
H2C
CH2
C NCH2
H2C
dodecanamide
pentan-3-ol
butane-1-thiol
N-ethyl-2-hexanamine
2-methoxyhexane
3-nitroheptane
H3C
H2C
CH
HC
CH2
H2C
CH2
CH2
CHCH2
H2C
CH2
H2CBr
hex-4Z-en-1-yneH2C
H2C
CH3
H2C
H3C
H2C
H3C
H2C
CH2
CH3
CCH2
O
Cl
H2CC
H2
H2C
CH2
H2C
CH2
H3C
H2C
CH3H3C
F
CH3
H2CH3C
C CH3CH2C
H2C
H2C
H2C
H2C
H2C
H2C CH3
H2CH3C
H2C N
O
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
CCH2
O
O
H2C
H2C
CCH2
O
NH2
H2CC
H2
CCH2
O
OH
H2C
CH2
H3C
nonanoyl chloride
pentanenitrile
octanal
nonan-4-one
dec-3E-ene
undec-2-yne
1-bromo-2-fluoroheptane
H3C CH2
CHCH2
CH3
OH
H3C OCHCH2
CH3
CH2
HN
CH
H2C C
H2CH3
H3C
H2C
CH2
H2C
SH
NCH
OO
H2C
H2C
1-nitrosobutane C C HH2C
HC
H3CH2C
CH3
H3C CH2
H2C
CH3
HC
CH3
H2C
CH2
H2C
CH2
H2C
CH2
H2C
H3C
CH3CH2
H3C
H2C
CH2
CH3
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups Key
pentanoic acidbutanoic anhydride
CCH2
O
O CO
CH2
CCH2
O
OH2C
H2C
ethyl pentanoate
CCH2
O
NH2
H2CC
H2
CCH2
O
CH2
H2CC
H2
H2C
CCH2
O
OH
H2C
CH2
H3C
CCH2
O
HH2CC
H2
H2CCH2
C NCH2
H2C
nonanoyl chloride
dodecanamide
pentanenitrile
octanal
nonan-4-one pentan-3-ol
b utane-1-thiol
N-ethyl-2-hexanamine
2-methoxyhexane
dec-3E-ene
undec-2-yne
1-bromo-2-fluoroheptane
3-nitroheptane
H3C CH2
CHCH2
CH3
OH
H3C OCHCH2
CH3
CH2
HN
CH
H2C C
H2CH3
H3C
H2C
CH2
H2C
SHH3C
H2C C
H
HC C
H2
H2C C
H2
CH2
CHCH2
H2C C
H2
H2CBr
NCH
OO
H2C
H2C
1-nitrosobutane hex-4Z-en-1-yne
H2C
C C HH2C
HC
H2C
CH3
H2C
H3C
H2C
H3C H3CH2C
CH3
H2C
CH2
CH3
CCH2
OCl
H2CC
H2
H2CCH2
H2CC
H2
H3CH3C C
H2
H2C
CH3
HC
CH3
H2C
CH2
H2C
CH2
H2C
CH2
H2C
H3C
CH3CH2
H3C
H2C
CH2
CH3
H2C
CH3H3C
F
CH3
H2CH3C
C CH3CH2C
H2C
H2C
H2C
H2C
H2C
H2C CH3
H2CH3C
H2C N
O
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
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
fluoro,chloro,bromo,iodo compounds
nitro compounds nitro compounds
alkenes alkynes
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups
carboxylic acids anhydrides esters
acid chlorides amides nitriles
aldehydes ketones alcohols
thiols amines ethers
thioethers / sulfides
fluoro,chloro,bromo,iodo compounds
nitro compounds nitro compounds
alkenes alkynes
CR
O
OH C
R
O
OC C
R
O
OR'
O
R
CR
O
Cl
CR
O
NH
CR
O
HC
R
O
R'
H
CR N
OR
SR
H
H
NR
H
H
OR
R'
SR
R'C C
RH
H H
CR C H
Cl Br
NR
O
ONR
O
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
Quiz on Functional Groups
Information and Examples
Primary carbon chain lengths (R = carbon chain)
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 = nonane10 carbons = decane11 carbons = undecane12 carbons = dodecane
Functional Groups Prefix (when lower priority) Suffix (when higher priority)*
1. carboxylic acids not used in our course -oic acid 2. anhydrides not used in our course -anhydride 3. esters (two parts) none for now alkyl -oate 4. acid chlorides none for now -oyl chloride 5. amides none for now -amide 6. nitriles cyano- -nitrile 7. aldehydes oxo- -al 8. ketones oxo- -one 9. alcohols hydroxy- -ol10. thiols mercapto- -thiol11. amines amino- -amine12. ethers (two parts) alkoxy- none13. thioethers (two parts) alkylthio- none14. alkenes none -ene15.alkynes none -yne16. halogen compounds fluoro-, chloro-, bromo-, iodo- none17. nitro compounds nitro- none18. nitroso- nitroso- 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.
Branch carbon chain lengths (drop "-ane" and add "-yl")
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 = nonyl10 carbons = decyl11 carbons = undecyl12 carbons = dodecyl
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 esters
acid chlorides amides nitriles
aldehydes ketones alcohols
thiols amines ethers
thioethers / sulfides fluoro, chloro, bromo, iodo compds nitro compounds
nitroso compounds
simple alkyl, alkenyl, alkynly chains
alkenes alkynes
C
O
OH
R
propanoic acid
C
O
OC
R
O
R
C
O
OC
H3C
O
CH3
ethanoic anhydride
C
O
OR'
R
C
O
OCH3CH2
H3Cmethyl propanoate
C
O
OH
CH2H3C
C
O
ClCH2H3C
C
O
ClR
propanoyl chloride
C
O
NH
R
H
propanamide (1o amide)
C
O
NH
CH2H3C
HC
CH2H3C
N
CR
N
propanenitrile
C
O
HCH2H3C
C
O
HR
propanal C
O
CH2CH2H3C CH3
C
O
RR
3-pentanone
R OH
CH2CH2H3C
OH1-propanol
R SH
CH2CH2H3C
SH1-propanthiol
R NH
H
CH2CH2H3C
NH21-propanamine
R OR'
1-ethoxypropane ethyl propyl ether
OCH2CH2
H3C CH2CH3
R SR'
1-ethylthiopropane ethyl propyl sulfide
SCH2CH2
H3C CH2CH3
F Cl Br I
3-bromo-5-chloro-7-fluoro-1-iodooctane
XR X = halogen NRO
O
NRO
Onitromethane
NRO
NRO
nitrosomethane
C CH
H
H
R
C C HR
C CH
H
H
H3CC C HH3Cpropene propyne
Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc
