Exam 3

Suffix of carboxylic acid

-oic acid

Name when carboxylic acid is attached to ring?

Alkane carboxylic acid

Suffix of 2 carboxylic acids

dioic acid

Structure of carboxylic acid

trigonal planar, strong H- bonding with more H bonding between acid pairs

Name of carboxylate ions

-oate

Acidity and pka

more acidic lower pka

Amide to Carboxylic Acid

H2O or H3O+

Nitrile to Amide

H2O or H3O+

Nitrile to Amine

LiAlH4 or 1. xs LAH 2. H2O

Nitrile to Ketone

RMgX

Alkane Halogen to Nitrile

NaCN

Amide to Nitrile

SOCL2, becomes dehydrated

Oxidative Cleavage of Alkynes

1. O3 2. H2O, alkyne to 2 carboxylic acids attached to R

Oxidation of Primary Alcohols

1. Na2Cr2O7, H2SO4 H2O, primary alcohol to carboxylic acid

Oxidation of Alkylbenzenes

1. Na2Cr2O7, H2SO4 H2O, side group alkane to carboxylic acid

Aldehyde to Carboxylic Acid

1. KMnO4/H2O, NaOH

Side group methyl on benzene to carboxlylic acid

1.KMnO4, H2O 95c

Nitrile to Carboxylic Acid

1. HCl, H2O 2. Heat

Carboxylation of Grignard

O=O + RMgBr -> Carboxylate ion -> H3O+

Nitriles to Iminies

RCN + RMgBr -> Imine anion + H2O -> Ketone + NH3

Carboxylic Acid to Primary Alcohol

1. LAH 2. H2O

Primary Alcohol to Carboxylic Acid

1. Na2Cr2O7, H2SO4, H2O

Acyl Chloride to Carboxylic Acid

1. H2O, Pyridine

Carboxylic Acid to Acyl Chloride

1. SOCl2

Acyl Chloride to Anyhydride

1. Carboxylic Acid, Pyridine

Acyl Chloride to Ester

1. ROH, Pyridine

Acyl Chloride to Amide

1. Excess NH3

Acyl Chloride to Aldehyde

1. LiAl(OR)3H 2. H2O

Acyl Chloride to Primary Alcohol

1. LAH 2. H2O

Anhydride to Carboxylic Acid

1. H2O

Anhydride to Ester

1. ROH

Carboxylic Acid to Anyhydride

1. Acyl Chloride, Pyridine

Ester to Carboxylic Acid

acid, H2O

Carboxylic Acid to Ester

acid, ROH

Ester to Amide

NH3

Amide to Amine

1. xs LAH 2. H2O

Ester to Aldehyde

1. DIBAH 2. H2O

Ester to Primary Alcohol

1. xs LAH 2. H2O

Side Group Halogen to Carboxylic Acid

1. Mg 2. CO2 3. H3O+

Derivatives of Carboxylic Acid

Acyl Chlorides, Esters, Amides, Acid Anhydrides