Functional Groups

Maggie Cheung SCH4U: Basic Functional Groups in Organic Chemistry

FUNCTIONAL GROUPS TO MEMORIZE PRIORITY: C A t s E a t A r m y A nts; K ittens A ttack A l l E nemy A r m y A n t s — A H ! N o A nts. ALSO: A m i d e before Ami n e & E s ter before E t h e r MELTING POINTS: Carboxylic Acid > Alcohol > Aldehydes/Ketones > Ester > Alkane TRANS/CIS (TACS): (e.g., transatlantic) transatlantic) Trans = Across (e.g., ORTHO/META/PARA: Ortho=Beside (1,2) Meta=Two away (1,3)

GROUP

DIAGRAM

NOMENCLATURE

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Carboxylic Acid -COOH

- Suffix, “-oic” or “-ic” acid - Prefix, “carboxy-”

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Ester -COOR

- Carbonyl group side = main c hain,

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Amide -CONH2

Aldehyde -CHO

suffix ““-oate” “-yl” - Side chain: suffix “- End result: “-yl  –oate”

- Suffix “-amide” - Secondary/tertiary: add “N-” location indicator at front or “N,N-“ if tertiary and name normally - Primary FG: suffix, “-al”. Don’t state location. - Otherwise: prefix, “ formyl-” in ring form or “oxo-” and state location

Cis = Same

Para=Opposite

PROPERTIES

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React: Aldehyde Ox./Red. Carbonyl (C=O) + Hydroxyl (C-OH) Several polar bonds MP: Carboxylic Acid > Alcohols Less than 5 Cs = soluble in water React: Alcohol + Carboxylic Acid Condensation/Hydrolysis Carbonyl (C=0) + Ester Bond (R-O-R’ (R-O-R’)) Polar bond MP: Carboxylic Acid > Alchol > Ester > Alkane React: Carboxylic Acid + Amine/Ammonia Acyll (R-C=O) + Nitrogen (N) Secondary, tertiary: 2 to 3 alkyl groups connected to N o React: 1 Alcohol Ox./Red. Terminal Carbonyl Group Partial Hydogen Bonding, DipoleDipole, 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 >CO

- Primary FG: suffix, “-one” - Otherwise: prefix, “ oxo-” - Always state location!

- React: 2o Alcohol Oxidation - Carbonyl Group - Cannot undergo Reduction

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Alcohol -OH

“ -ol” - Primary FG: add suffix, “- Otherwise: prefix, “ hydroxy- Isopropanol: OH in middle.

- React: Alkene addition/dehydra. or

end—primary Propanol: OH at end—

Alkyl Halide substitution/dehydra - Polar bond. Both acid and base - Reciprocal Hydrogen Bonding

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Maggie Cheung SCH4U: Basic Functional Groups in Organic Chemistry alcohol.

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Amine -NH2

Ether -O-

- Side chain location indicator of  -

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Alkene C=C

-

-

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“N“ on each one Main chain suffix “( #)-amine” Prefix “amino-“ Larger alkyl group (or group with functional group) is root “-yl – yl yl ether” or “-oxy (other  side)” Stereoisomers: trans- or cisbecause bond cannot rotate and there are 2 possible locations for Groups to bond Rings: cycloTert-, Iso#C where found or root chain + “ ene” or “alkenyl-”

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Primary: end alcohol; no location Secondary: two other carbons Tertiary: three other carbons MP: Alcohol>Alkane React: Akyl Halide substit./dehydra. Ammonia derivative, H atoms replaced by substituents, e.g. alkyl groups

- React: Alcohol condens/dehydra. - C-O polar bond; Dipole-Dipole and partial Hydrogen Bonding - MP: Alcohol>Ether>Alkane - Benzene! Aromatic molecule! Resonance!

Alkyne C≡C Alkyl Halide -X Nitro -NO+

- #C found at or root chain + “ -yne” - “alkynyl-“ - Smallest numbers for Halogens.

Alkane C-C

- Find longest C chain. Identify 

bonds —can rotate=no - Only single bonds—

branches/side chains. Number Cs according to priority. Locate double/triple bonds. Alphabetize. Combine name. - C# or root chain + “-ane” or “alkyl”

stereoisomers - CnH2n+2 - Only London Forces; MP increases with size

Alphabetically for priority amongst. - Prefix: “nitro-”

- Triple bond; only one remaining bond on each side = no trans/cis

-

- Resonance in molecule between two Os (indistinct “electron cloud”)

ROOT CHAIN NAMES #C 1 2 3 4 5 6 7

PREFIX MethEthPropButPentHexHept-

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Maggie Cheung SCH4U: Basic Functional Groups in Organic Chemistry

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OctNonDec-

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