Carboxylic Acids and Derivatives Nomenclature (ch. 20.1+.2+.6)

name these molecules (use common name for first one)

common name?

common name?

formic acid

common name?

acetic acid

Common name?

propionic acid

Common name?

Butyric acid

what naming scheme indicate a monocarboxylic acid?

what number locant is the carboxylic acid assigned?

suffix “oic acid”
when is this suffix used?

1

when a carboxylic acid is attached to a ring, what suffix is used?

“carboxylic acid”

when is this suffix used?

name?

cyclohexanecarboxylic acid

what naming scheme indicated a dicarboxylic acid?

suffix “dioic acid”

what does this suffix indicate?

anagram for common dicarboxylic acids?

Oh My, Such Good Apple Pie

Oxalic, Malonic, Succinic, Glutaric

(we don’t care about the apple pie part in this class)

common name?

oxalic acid

common name?

malonic acid

common name?

succinic acid

common name?

glutaric acid

name this molecule

(do not use the common name)

pentanedioc acid

What are carboxylate salts?

How are they named?

ions formed by deprotonation of a carboxylic acid

replace the suffix “ic aid” with “ate”

name?

sodium benzoate

what is a carboxylic acid derivative?

any compound where carbon has three bonds to electronegative atoms.

what are the four most common CA derivatives?

(name and draw them)

what does Z indicate?

Z

heteroatoms (Cl, O, N, etc.)

how do you indicate heteroatoms on a molecule?

what is a heteroatom?

any atom that is not Carbon or Hydrogen

which CA derivatives are less common in nature?

(they are unstable)

acid halides and anhydrides

why are these two CA derivatives less common in nature?

Which CA derivatives are abundant in nature?

(they are more stable)

Amides and esters

why are these two CA derivatives abundant in nature?

draw the general structure of a protein

resonance

why are proteins stable?

how to name an acid halide?

suffix “yl halide” replaces “ic acid” (keep the o from “oic” on IUPAC names)

draw benzoyl acid

name?

draw acetyl bromide

name?

when an acid halid group is attached to a ring, what suffix is used?

carbonyl halide

when is this suffix used?

name?

cyclohexanecarbonyl choride

how to name symmetrical anhydrides?

replace suffix “acid” with “anhydride”. basically name only one side of the molecule.

name?

acetic anhydride

name?

succinic anhydride

how to name asymmetrical anhydride?

named by listing acid alphabetically, followed by “anhydride”

name?

acetic benzoic acid anhydride

how to name esters?

how to name esters on a ring?

name the alkyl group attached to the oxygen, follwoed by the carboxylic acid’s name with the suffix “ate” instead of “ic acid”

same rules apply for naming them on a ring.

name?

ethyl acetate

name?

diethyl malonate

name?

methyl cycolhexanecarboxylate

how to name amides? (with no substituents)

replace suffix “ic acid” or “oic acid” with “amide”

name?

acetamide

name?

benzamide

how to name amide group attached to a ring

replace “carboxylic acid” with “carboxamide”

cyclohexanecarboxamide

how to name an amide with alkyl substiuents?

substituent names are placed at the beginning of the name (like they are substituents on a hydrocarbon chain), and their locant is indicated as N

name?

N,N-dimethylacetamide

name?

N-methylacetamide

how to name nitriles?

replace suffix “ic acid” or “oic acid” with “onitrile”

name

acetonitrile

name?

benzonitrile

Most CA derivatives have a carbonyl group. Name and draw the CA derivative without a carbonyl group (the one we discuss).

what makes this CA derivative special?

Draw DMF.

N,N dimethylformamide

name this molecule