"Master Organic Chemistry" Note - this sheet is not meant to be comprehensive.

Your course
Summary Sheet - Functional Groups (1) masterorganicchemistry.com may provide additional material, or may not cover some of the
reactions shown here. Your course instructor is the final authority.
August 2012 Version 1.1
What Are Functional Groups?
δ– δ+ The OH group is an alcohol [unless OH is attached to C=O,
Functional groups are collections of atoms that have a common pattern of chemical Alcohol R O H in which case it's a carboxylic acid (below)]
reactivity O δ− A carbonyl (C=O) attached to a hydrogen
Aldehyde +
Suffix: "-ol". As a substituent: "hydroxy" Cδ and another carbon is an aldehyde
R H
Alkane C a hydrocarbon with no multiple bonds is an alkane
Examples: OH OH Suffix: "-al" (if attached to ring: carbaldehyde) As a substituent: "oxo"
OH OH
H3C Examples:
Suffix: "-ane". As a substituent: "alkyl" O
Examples: O
Methanol Ethanol 2-propanol ("Isopropanol") 2-methyl-2-propanol O O
a primary alcohol a secondary alcohol (t-butanol) C H
H2 H3C H
C ( ) a tertiary alcohol H H
H3C CH3 8
Characteristics: polar (O-H group participates in hydrogen bonding) Ethanal Propanal Butanal Benzaldehyde
Propane Butane Decane 2-methylpentane Reactivity: acid-base reactions (can act as acids or bases) Characteristics: the C=O bond is somewhat polar
Characteristics: nonpolar substitution reactions (can act as nucleophiles) Reactivity: addition reactions (the carbonyl carbon reacts easily with nucleophiles)
Geometry: tetrahedral (sp3 hybridized) oxidation reactions (primary and secondary alcohols (and methanol)
can be oxidized to aldehydes, ketones, or carboxylic acids, depending
Reactivity: free radical reactions (e.g. free radical chlorination or bromination) on structure and reagent used) O δ− A carbonyl (C=O) flanked by two carbons
Ketone +
Cδ is a ketone
a hydrocarbon with at least one C–C double R R
Alkene C C bond (π bond) is an alkene δ– δ+
An oxygen flanked by two carbons is an ether Suffix: "-one". As a substituent: "oxo"
Ether R O R
Suffix: "-ene". As a substituent: "alkenyl" Examples: O
Examples: As a substituent: "alkoxy" O O O
C
H3C H Examples: O H3C CH3
C C O
H H H3C CH3 O
O 2-propanone 2-butanone 3-hexanone phenyl methyl ketone
("acetone") ("methyl ethyl ketone") ("acetophenone")
Propene trans-2-butene cis-2-butene (E)-3,5-dimethylhex-2-ene Dimethyl ether Ethyl methyl ether Methyl phenyl ether Tetrahydrofuran (THF)
[or (E)-2-butene] [or (Z)-2-butene] (or "methoxyethane") (or "methoxybenzene", a cyclic ether Characteristics: the C=O bond is somewhat polar (less so than O-H however)
Characteristics: nonpolar. Molecule cannot rotate along double bond. or "anisole")
Reactivity: addition reactions (the carbonyl carbon reacts easily with nucleophiles)
Geometry: trigonal planar (sp2 hybridized) acid-base reactions (carbons adjacent to the ketone can be deprotonated
Characteristics: borderline between nonpolar and polar (due to dipole-dipole)
Reactivity: undergo addition reactions, as well as oxidative cleavage to give enolates)
Stability increases with increasing # of carbons attached Reactivity: acid-base reactions (oxygen can act as a very weak base

a hydrocarbon with at least one C–C – – – – O δ−

Alkyne C C δ+ δ δ+ δ δ+ δ δ+ δ An alkyl group attached to + δ+ A carbonyl (C=O) adjacent to a hydroxyl
triple bond (π bond) is an alkyne Alkyl halide R F R Cl R Br R I a halogen is an alkyl halide Carboxylic acid Cδ H (OH) and an R group is a carboxylic acid
R O −
δ
Suffix: "-yne". As a substituent: "alkynyl"
Suffix: "-ane". As a substituent: "haloalkyl" Suffix: "-oic acid"
Examples: Examples:
Examples: O
Cl O O O
H3C C C H Br
C OH
I F H OH OH
Propyne 2-butyne 3-heptyne H3C
a terminal alkyne
Iodomethane Fluoroethane 2-chloropropane 2-methyl-2-bromopropane Methanoic acid Ethanoic acid Butanoic acid benzoic acid
(methyl iodide) (ethyl fluoride) (isopropyl chloride) (t-butyl bromide) ("formic acid") ("acetic acid")
Alkynes with a C–H bond are called "terminal" alkynes
a primary alkyl a secondary alkyl halide a tertiary alkyl halide Reactivity: acid-base reactions (the O–H is acidic)
Geometry: linear (sp hybridized) halide acyl substitution reactions (can replace OH with other groups under
Characteristics: non polar Characteristics: generally considered non polar (but more polar than alkanes) acidic conditions)
Reactivity: addition reactions Reactivity: substitution reactions (Cl, Br, I can be good leaving groups)
oxidative cleavage reactions elimination reactions (Cl, Br, I can be good leaving groups) O δ−
acid-base reactions (terminal alkynes are unusually acidic) + A carbonyl (C=O) adjacent to an alkoxy
Ester Cδ (OR) and an R group is an ester
R O R
δ– δ+ A nitrogen attached to simple carbon or
A six-membered ring containing Amine
Benzene ring 3 alternating double bonds is a R N H hydrogen atoms is an amine
H Suffix: "-oate"
benzene ring
Examples: O
Suffix: "benzene". As a substituent: "phenyl" Suffix: "-ine". As a substituent: "amino"
O O O
Examples:
Examples: H C O
N N H OCH3 O O
NH2 NH2
H3C
Methyl methanoate Methyl ethanoate Ethyl butanoate Methyl benzoate
Methylamine Ethylamine Dimethylamine Triethylamine
a primary amine a secondary amine a tertiary amine Reactivity: acyl substitution reactions (can replace OR with other functional
Benzene Methylbenzene 1,4-dimethylbenzene groups under acidic conditions)
(toluene) (para-dimethylbenzene) Characteristics: polar (N-H group participates in hydrogen bonding, although not as addition reactions (the carbonyl carbon reacts easily with nucleophiles)
much as a hydroxy group
Reactivity: acid-base reactions (tend to act as bases) Omissions, Mistakes, Suggestions?
Reactivity: substitution reactions (e.g. electrophilic aromatic substitution substitution reactions (can act as nucleophiles)
or nucleophilic aromatic substitution)
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Less reactive than normal alkenes due to aromatic stability
This sheet copyright 2012, James A. Ashenhurst
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