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 O

4S
C

2Z 1

6 7
H

4 5
H

3 2

OH

2 3 4 2 Notice that no "1" is used for the carboxylic acid group, because it has to be "1" in this structure.

(2Z,4S)-3-ethoxy-4-methyl-8-oxooct-2-en-6-ynoic acid
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Quiz on Functional Groups

Functional Group
O

prefix
R C O O C R

suffix alkanoic acid alkanoic anhydride (if symmetrical) alkyl alkanoate (R') (RCO2) alkanoyl chloride "R" = carbon chains alkanamide alkanenitrile alkanal #-alkanone #-alkanol #-alkanethiol # carbons 1 2 3 4 5 6 7 8 9 10 11 12 alkane chain name methane ethane propane butane pentane hexane heptane octane nonane decane undecane dodecane alkyl branch name methyl ethyl propyl butyl pentyl hexyl heptyl octyl nonyl decyl undecyl dodecyl The part of each name specific to the functional group is in bold and underlined to help you see those features.

1. Carboxylic acid 2. Anhydride

R O C O R C O R C O R C O

not considered
OH

not considered not considered #-chlorocarbonyl

3. Ester 4. Acid halide 5. Amide 6. Nitrile 7. Aldehyde

R

R'

Cl

#-carbamoyl
NH2

R C N O C O R C R'

#-cyano #-oxo

8. Ketone 9. Alcohol 10. Thiol 11. Amine 12. Ether 12. Halogen 12. Azide* 12. Diazo* 12. Nitro* 12. Nitroso 12. Carbon branches

#-oxo (older = #-keto) #-hydroxy #-mercapto #-amino

R OH

R SH

R NH2

#-alkylamine / #-alkanamine

R O R'

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 #-azido #-diazo #-nitro #-nitroso #-alkyl, #-(alk-#-enyl), #-(alk-#-ynyl) always prefixes (no suffix names)

R N3

R N2

R NO2

R NO

* = 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 -ene -yne high priority suffix see list above

branches and see box above low priority functional groups

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Quiz on Functional Groups

A = carboxylic acid

B = anhydride

C = acid chloride

D = ester

E = amide

CH3CO2H

CH3CO2COCH3

CH3COCl

CH3CO2CH3

CH3CONH2

F = nitrile

G = aldehyde

H = ketone

I = alcohol

J = ether

K = thiol

CH3CN

CH3CHO

CH3COCH3

CH3CH2OH

CH3OCH3

CH3CH2SH

L = sulfide / thioether M = amine (1o,2o,3o)

N = bromoalkane CH3N(CH3)2 3
o

O = alkene

CH3SCH3

CH3CH2NH2 1
o

CH3NHCH3 2
o

CH3CH2Br

CH2CHCH3

P = alkyne
CH3CCH

Q = alkane CH2CHCH3

R = nitroalkane

S = nitrosoalkane

T = diazoalkane

CH3CH2NO2

CH3CH2NO

CH2NN

A = carboxylic acid
O C H3C OH

B = anhydride
O C H3C O O C CH3

C = acid chloride
O C H3C Cl

D = ester
O C H3C O CH3

E = amide
O C H3C NH2

F = nitrile

G = aldehyde
O

H = ketone
O

I = alcohol
H3C OH C H2

J = ether
O H3C CH3

K = thiol
H3C C H2 SH

H3C

N H3C

C H H3C

C CH3

L = sulfide / thioether M = amine (1o,2o,3o)

H3C S H3C CH3 H3C C H2 NH2 H3C N H CH3 N CH3 CH3

N = bromoalkane
H2 C H3C Br

O = alkene
H C H2C CH3

P = alkyne
H3C C C H

Q = alkane
H3C C H2 CH3

R = nitroalkane
O

S = nitrosoalkane

T = diazoalkane

H3C H3C C H2 N O C H2

N O

H2C

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Quiz on Functional Groups

Match the name and functional group with the proper structure.
A Names 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 Letter _____ _____ _____ _____ _____ _____ _____
C H3C C H2 C O H3C H2 C C H2 H2 C C H2 CH3 H3C

H2 C C H2

C
O C H2 CH3 H3C C H2

O C OH

O H2 C CH3

E
H2 C H3C C H2

O C NH2

F
H2 C H3C C H2 H2 C Br

O H2 C C H2 CH3

H
H3C

H2 C C C H

I
H3C

H2 C C H

H C CH3

J
H2 C H3C C H2

O C H

_____ _____ _____ _____ _____ _____ _____ _____ _____

H3C

O C

O C O CH3

L
H3C

H2 C CH OH

H2 C C H2

M
CH3 H3C H2 C C H2 NH2

H3C

N
H3C C H2

O C Cl

O
H3C C H2 H2 C CH SH CH3

P
H3C C H2 H2 C C H2 H2 C C N

Possible Solutions:
E C
H3 C C H2 O C OH H3C

O C O

O C CH3

D
H3C C H2

O C O H2 C CH3

N
H3 C C H2

O C Cl H3 C H2 C C H2

O C NH2

carboxylic acid propanoic acid P

H3C C H2 H2 C C H2 H2 C C

anhydride ethanoic anhydride J

H2 C H3C N C H2 O C H

ester ethyl propanoate G

O C H3C H2 C C H2 CH3

acid chloride propanoyl chloride L

H3C H2 C CH OH

amide butanamide
H2 C C H2

CH3

nitrile hexanenitrile O
H3 C C H2 H2 C CH SH CH3

aldehyde butanal M
H3 C H2 C C H2

ketone pentan-2-one B
H2 C C H2

alcohol hexan-3-ol F
O C H2 CH3 H3C H2 C C H2

NH2 H3C

H2 C Br

thiol pentane-2-thiol I
H3 C H2 C

amine propan-1-amine H
CH3 H3 C H2 C C C

ether 1-ethoxypropane A
H3 C H H2 C C H2 H2 C C H2

"halo" alkane 1-bromobutane

CH3

H C C H

alkene pent-2E-ene

alkyne but-1-yne

alkane hexane

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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.
A B C
OH OH

D
NH2

NH2

NH2

G
Br

J
N N H

K
F

L
H N

Cl

OH

P
NH2 N

A 3
o

1o, methyl

4o B allyl, 2o, methylene C allyl, 2o, methylene D 1o alcohol 1o amine

vinyl vinyl
OH OH NH2

3o alcohol E
O

2o, methylene

allyl, 3o, methine

2o, methylene 1o, methylene H 2o, methine I

O

methine methyl

F 1 , methyl
o

G 4o

1o, methylene
Br
o

3o, methine
NH2 N H

NH2

1 amide J
N

1 amine K

1o RX compound
F

2 RX compound L
H N

Cl

1o, methyl M

2 amide

4o ammonium ion

1o, methylene

OH

1o, methylene

3o RX compound

2o amine

2o alcohol, methine

benzyl, methylene

1o, methyl

P
NH2 N

benzyl, methyl

3o amine 3o, methine phenyl position 3o amide methyl 2o, methylene 3o 1 amine
o

1o, methylene 2o, methylene

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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 2. isopropyl X
X X X X 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

X X X

I
X

J
X

M
X

N
X

11. phenyl X 12. benzyl X 13. neoheptyl X 14. t-hexyl X

Answers:
A B
X X X

E
X

F
X

sec-butyl X H

benzyl X

neopentyl X I
X

isobutyl X J

n-propyl X K
X

vinyl X

n-butyl X L
X

phenyl X M
X

t-butyl X N

allyl X

t-hexyl

neoheptyl X

isopropyl X

propargyl X

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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 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 N
H3C C H2 H2 C C H2 O C NH2

Letter _____ _____ _____ _____ _____ _____ _____ _____ _____ _____ _____ _____ _____ _____

A
H3C

H2 C C H2

H2 C C H2

H2 C C H2

B
CH3 H3C H2 C C H2 H2 C C H2 H2 C C H2 H2 C C H2

O C OH

O C H2 C O C H2 CH3

D
O H3C C H2 O H2 C C H2 H2 C C H2 C NH2

E
H2 C H3C C H2 H2 C Br

H3C

F
H2 C H3C C H2 O C H3C O O C CH3 H2 C C H2

G
H2 C O CH3 H3C C H2 O C H2 CH3

H
O C H3C C H2 O H2 C C H2 C H2 H2 C C H2 O H2 C H3C C H2 H2 C C H2 H2 C C H2 C H C Cl H2 C CH3

J
H2 C H3C C H2

O C OH

K
H3C

L
H2 C H3C C H2 H2 C CH SH H2 C CH3

_____ _____ O
H2 C H3C C H2

P
H2 C C C H H3C H2 C C H2 O C H2 H2 C CH3

Q
H2 C H3C C H2 O H2 C H3C NH2 C H2 C H H2 C C H

CH2

R
H3C C H2 H2 C C H2 H2 C C N

S
H3C Br

T
H3C C H2 H2 C C H2 H2 C C H2 H2 C CH CH3

V
H3C C H2

O C O

O C C H2 CH3

W
H3C C H2 H2 C C H2

O C Cl

X
H3C

H2 C C H2

H2 C C H2

H2 C CH OH

H2 C C H2

CH3

Y
H2 C CH2 C H

H3C O

Z
H3C C H2 H2 C C H2 H2 C C H2 H2 C C H2 H2 C CH NH2 CH3

AA
H2 C H3C CH OH H2 C CH SH CH3 H2 C C H2 CH3

BB
H2 C H3C C H2 H2 C C H2

C C H2

H2 C CH3

CC
H3C C H2 H2 C C H2 H2 C C H2 H2 C C H2 H2 C

DD
H3C C H2

EE
H2 C C H2 H2 C C H2 H2 C C N H3C C C H CH4

FF

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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 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 N
H3C C H2 H2 C C H2 O C NH2

Letter __B__ __I__ __F__ __K__ __N__ _DD_ __U__ _BB_ _AA_ __Z__ __P__ _CC_ __S__ __Q__

A
H3C

H2 C C H2

H2 C C H2

H2 C C H2

B
CH3 H3C H2 C C H2 H2 C C H2 H2 C C H2 H2 C C H2

O C OH

O C H2 C O C H2 CH3

D
O H3C C H2 O H2 C C H2 H2 C C H2 C NH2

E
H2 C H3C C H2 H2 C Br

H3C

F
H2 C H3C C H2 O C H3C O O C CH3 H2 C C H2

G
H2 C O CH3 H3C C H2 O C H2 CH3

H
O C H3C C H2 O H2 C C H2 C H2 H2 C C H2 O H2 C H3C C H2 H2 C C H2 H2 C C H2 C H C Cl H2 C CH3

J
H2 C H3C C H2

O C OH

K
H3C

L
H2 C H3C C H2 H2 C CH SH H2 C CH3

__O__ __A__ O
H2 C H3C C H2

P
H2 C C C H H3C H2 C C H2 O C H2 H2 C CH3

Q
H2 C H3C C H2 O H2 C H3C NH2 C H2 C H H2 C C H

CH2

R
H3C C H2 H2 C C H2 H2 C C N

S
H3C Br

T
H3C C H2 H2 C C H2 H2 C C H2 H2 C CH CH3

V
H3C C H2

O C O

O C C H2 CH3

W
H3C C H2 H2 C C H2

O C Cl

X
H3C

H2 C C H2

H2 C C H2

H2 C CH OH

H2 C C H2

CH3

Y
H2 C CH2 C H

H3C O

Z
H3C C H2 H2 C C H2 H2 C C H2 H2 C C H2 H2 C CH NH2 CH3

AA
H2 C H3C CH OH H2 C CH SH CH3 H2 C C H2 CH3

BB
H2 C H3C C H2 H2 C C H2

C C H2

H2 C CH3

CC
H3C C H2 H2 C C H2 H2 C C H2 H2 C C H2 H2 C

DD
H3C C H2

EE
H2 C C H2 H2 C C H2 H2 C C N H3C C C H CH4

FF

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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
O H C OH

anhydrides
O C O C

esters
H3C O C CH3

H3C

CH3

C H2

methanoic acid acid chlorides

H2 C O C

ethanoic anhydride amides

H3C H2 C O C

methyl propanoate nitriles

H3C H2C C N

H3C

C H2

Cl

C H2

C H2

NH2

butanoyl chloride aldehydes

H2 O H2C C C C H C H3C H2 H2

pentanamide ketones
H3C H2 C O C H2 C CH3

propanenitrile alcohols
H2 C OH CH CH3 C C H2 H2

C H2

H3C

hexanal thiols
H3C H2 C C H2 H2 C C H2 H2 C C H2 H2 C SH

hexan-2-one amines
H N H2 C

hexan-3-ol ethers
H2 C CH3 CH O CH3

H3C

CH

CH3

H3C

CH3

octane-1-thiol alkenes
H2 C H C H2 C

N-methyl-2-butanamine alkynes
H3C H2C C C CH3

2-ethyxypropane fluoro,chloro,bromo,iodo compounds

Br C H2 H2 C C H2 H2 C C H2 Cl

H3C

C H

C H2

CH3

hept-3E-ene alkenyne
H2C C H H2 C C C CH3

pent-2-yne nitro compounds

H3C O CH N O H3C

1-bromo-5-chloropentane nitroso compounds

H3C O CH N H3C

hex-1-en-4-yne

2-nitropropane

2-nitrosopropane

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Quiz on Functional Groups

Name ______________________________ Nomenclature #1 - Provide a name for the structures and a structure for the names.
H2 C O C O C H2 C

pentanoic acid
CH3

H3C

C H2

C H2

H3C

H2 C

C H2

H2 C

C H2

H2 C

C H2

O C

N-ethyl-2-hexanamine
H

H3C

H2 C

C H

H C

C H2

H2 C

C H2

H2 C

C H2

CH3

butane-1-thiol

H3C

C H2

H2 C

C H2

H2 C

C H2

H2 C

C H2

O C

3-nitroheptane
Cl

H3C

O H2 H2 H2 C C C N

hex-4Z-en-1-yne

H3C

H2 H2 H2 H2 H2 H2 H2 C C C C C C C CH3

dodecanamide

H3C

H2 H2 C C C C N H2

ethyl pentanoate

F Br CH C C H2 H2 H2 C C H2 H2 C CH3

2-methoxyhexane

H2 C H3C

C H2

H2 C

O C H2 C C H2

H2 C CH3

pentan-3-ol

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Quiz on Functional Groups

Name ______________________________ Nomenclature #2 - Provide a name for the structures and a structure for the names.

butanoic anhydride
H3C C H2

H2 C

C H2

O C

OH

octanal
H3C

C H2

H N

H2 H2 C C CH C CH3 H CH 2
3

dec-3E-ene
H3C

H2 C

C H2

H2 C

SH

nonanoyl chloride

H2 H2 H2 C C C CH H3C C CH3 H2 N O O H C HC CH3 H2 C C C H

1-nitrosobutane

undec-2-yne
H3C

H2 C

C H2

H2 C

C H2

H2 C

C H2

H2 C

H2 O C C C C NH2 H2 H2

pentanenitrile
H3C

H2 O H2 C C C C O C CH3 H2 H2

1-bromo-2-fluoroheptane
H3C

CH3 H2 CH3 CH C C O C H2 H2

nonan-4-one

H3C

OH CH CH3 C C H2 H2

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Quiz on Functional Groups

Key

butanoic anhydride
H3C H2 C C H2 O C O O C C H2 H2 C CH3

pentanoic acid
H3C C H2 H2 C C H2 O C OH

octanal
H2 H2 O C H2C C C C C H H3C C H2 H2 H2

N-ethyl-2-hexanamine
H3C C H2 H N H2 H2 C C CH C CH3 CH H2
3

dec-3E-ene
H2 H H2 C C C H3C C C C H H2 H2 H2 C C H2 CH3

b utane-1-thiol
H3C H2 C C H2 H2 C SH

nonanoyl chloride
H2 H2 O H3C C H2C C C C C C C Cl H2 H2 H2 H2

3-nitroheptane
H2 H2 H2 C C C CH H3C C CH3 H2 N O O

1-nitrosobutane
H2 H2 H2 O H3C C C C N

hex-4Z-en-1-yne
HC

H C CH3

H2 C C C H

undec-2-yne
H2 H2 H2 H2 H2 H2 H2 H3C C C C C C C C C C CH3

dodecanamide
H3C H2 C C H2 H2 C C H2 H2 C C H2 H2 C H2 O C C C C NH2 H2 H2

pentanenitrile
H2 H2 H3C C C C C N H2

ethyl pentanoate
H3C H2 O H2 C C C C O C CH3 H2 H2

1-bromo-2-fluoroheptane
Br F CH H2 H2 C C C C CH3 H2 H2

2-methoxyhexane
H3C CH3 H2 CH3 CH C C O C H2 H2 OH CH CH3 C C H2 H2

C H2

nonan-4-one

H2 H2 H2 O C C C C C C C CH3 H3C H2 H2 H2

pentan-3-ol
H3C

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

alkenes

alkynes

fluoro,chloro,bromo,iodo compounds

nitro compounds

nitro compounds

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Quiz on Functional Groups

carboxylic acids
O C R O H

anhydrides
O C R O O C R

esters
O C R O R'

acid chlorides
O

amides
O C H N H

nitriles

C R Cl

aldehydes
O C R H

ketones
O C R R'

alcohols
H R O

thiols
H R S

amines
H R N H

ethers
R' R O

thioethers / sulfides
R' R S

alkenes
H C H C H R

alkynes

fluoro,chloro,bromo,iodo compounds

nitro compounds
O

nitro compounds
O

R Cl Br

N R O N

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 = nonane 10 carbons = decane 11 carbons = undecane 12 carbons = dodecane Functional Groups 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 = nonyl 10 carbons = decyl 11 carbons = undecyl 12 carbons = dodecyl

Prefix (when lower priority) Suffix (when higher priority)* -oic acid -anhydride -oate -oyl chloride -amide -nitrile -al -one -ol -thiol -amine none none -ene -yne none none none

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-

*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 R O H 3C CH2 C O H propanoic acid O R O H 3C CH2 C propanoyl chloride Cl O R O H 3C thiols R S CH2 C H propanal H 3C CH2 C H O C CH3 CH2 3-pentanone H R N H H 3C H 3C CH2 CH2 SH 1-propanthiol H 3C CH2 CH2 NH2 1-propanamine CH2 O CH2 CH2 CH3 1-ethoxypropane ethyl propyl ether O R X F Cl X = halogen Br I R N 3-bromo-5-chloro-7-fluoro-1-iodooctane alkenes H C R H nitrosomethane C H 3C C H H propene H 3C C C H propyne C H H alkynes R C C H O O nitromethane R N O ethers R O H 3C CH2 CH2 OH 1-propanol ketones R C Cl O H 3C CH2 C N H O C R H propanamide (1o amide) H 3C CH2 C H3C O C O H O C O O C ethanoic anhydride CH3 O R C N H N propanenitrile H H 3C CH2 anhydrides R O C O O C R O C O CH3 methyl propanoate N esters R O C O R'

acid chlorides

amides

nitriles R C

aldehydes

alcohols H R O

amines H

R'

thioethers / sulfides R H 3C S CH2 CH2 S

R'

fluoro, chloro, bromo, iodo compds

nitro compounds

CH2

CH3 1-ethylthiopropane ethyl propyl sulfide O

nitroso compounds R N O R N

simple alkyl, alkenyl, alkynly chains

Z:\classes\314\314 Special Handouts\nomen quiz on FGs.doc