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Maggie Cheung 1

SCH4U: Basic Functional Groups in Organic Chemistry

FUNCTIONAL GROUPS
TO MEMORIZE PRIORITY:
CAts Eat Army Ants; Kittens Attack All Enemy Army Ants—AH! No Ants.
ALSO:
Amide before Amine & Ester before Ether

MELTING POINTS:
Carboxylic Acid > Alcohol > Aldehydes/Ketones > Ester > Alkane

TRANS/CIS (TACS):
Trans = Across (e.g., transatlantic) Cis = Same

ORTHO/META/PARA:
Ortho=Beside (1,2) Meta=Two away (1,3) Para=Opposite

GROUP DIAGRAM NOMENCLATURE PROPERTIES


1 Carboxylic - Suffix, “-oic” or “-ic” acid - React: Aldehyde Ox./Red.
Acid - Prefix, “carboxy-” - Carbonyl (C=O) + Hydroxyl (C-OH)
-COOH - Several polar bonds
- MP: Carboxylic Acid > Alcohols
- Less than 5 Cs = soluble in water
2 Ester - Carbonyl group side = main chain, - React: Alcohol + Carboxylic Acid
-COOR suffix “-oate” Condensation/Hydrolysis
- Side chain: suffix “-yl” - Carbonyl (C=0) + Ester Bond (R-O-R’)
- End result: “-yl –oate” - Polar bond
- MP: Carboxylic Acid > Alchol > Ester >
Alkane
3 Amide - Suffix “-amide” - React: Carboxylic Acid +
-CONH2 - Secondary/tertiary: add “N-” Amine/Ammonia
location indicator at front or - Acyll (R-C=O) + Nitrogen (N)
“N,N-“ if tertiary and name - Secondary, tertiary: 2 to 3 alkyl groups
normally connected to N
4 Aldehyde - Primary FG: suffix, “-al”. Don’t - React: 1o Alcohol Ox./Red.
-CHO state location. - Terminal Carbonyl Group
- Otherwise: prefix, “formyl-” in ring - Partial Hydogen Bonding, Dipole-
form or “oxo-” and state location Dipole, highly polar
- MP: Alcohols > Carbonyl Groups >
everything else
- Less than 5 C’s = soluble in water.
More than 5C’s = insoluble in water.
5 Ketone - Primary FG: suffix, “-one” - React: 2o Alcohol Oxidation
>CO - Otherwise: prefix, “oxo-” - Carbonyl Group
- Always state location! - Cannot undergo Reduction
6 Alcohol - Primary FG: add suffix, “-ol” - React: Alkene addition/dehydra. or
-OH - Otherwise: prefix, “hydroxy- Alkyl Halide substitution/dehydra
- Isopropanol: OH in middle. - Polar bond. Both acid and base
Propanol: OH at end—primary - Reciprocal Hydrogen Bonding
Maggie Cheung 2
SCH4U: Basic Functional Groups in Organic Chemistry

alcohol. - Primary: end alcohol; no location


- Secondary: two other carbons
- Tertiary: three other carbons
- MP: Alcohol>Alkane
7 Amine - Side chain location indicator of - React: Akyl Halide substit./dehydra.
-NH2 “N“ on each one - Ammonia derivative, H atoms replaced
- Main chain suffix “(#)-amine” by substituents, e.g. alkyl groups
- Prefix “amino-“
8 Ether - Larger alkyl group (or group with - React: Alcohol condens/dehydra.
-O- functional group) is root - C-O polar bond; Dipole-Dipole and
- “-yl –yl ether” or “-oxy (other partial Hydrogen Bonding
side)” - MP: Alcohol>Ether>Alkane
9 Alkene - Stereoisomers: trans- or cis- - Benzene! Aromatic molecule!
C=C because bond cannot rotate and Resonance!
there are 2 possible locations for
Groups to bond
- Rings: cyclo-
- Tert-, Iso-
- #C where found or root chain + “-
ene” or “alkenyl-”

10 Alkyne - #C found at or root chain + “-yne” - Triple bond; only one remaining bond
C≡C - “alkynyl-“ on each side = no trans/cis
11 Alkyl - Smallest numbers for Halogens. -
Halide Alphabetically for priority
-X amongst.
12 Nitro - Prefix: “nitro-” - Resonance in molecule between two
-NO+ Os (indistinct “electron cloud”)

13 Alkane - Find longest C chain. Identify - Only single bonds—can rotate=no


C-C branches/side chains. Number Cs stereoisomers
according to priority. Locate - CnH2n+2
double/triple bonds. Alphabetize. - Only London Forces; MP increases
Combine name. with size
- C# or root chain + “-ane” or “alkyl”

ROOT CHAIN NAMES


#C PREFIX
1 Meth-
2 Eth-
3 Prop-
4 But-
5 Pent-
6 Hex-
7 Hept-
Maggie Cheung 3
SCH4U: Basic Functional Groups in Organic Chemistry

8 Oct-
9 Non-
10 Dec-