Exam 3 Flashcards
Functional Group: Carboxylic Acid
Reaction Conditions: As an acid, with
NaOH
What Happens: Creates an anion w/ Na+, H2O
Alternatives: NaHCO3 (also makes CO2)
Functional Group: Carboxylic Acid
Reaction Conditions: 1) LiAlH4, 2)H3O+
What Happens: Completely reduced double bond w/O to 2 H bonds
Alternatives: N/A
Functional Group: Carboxylic Acid
Reaction Conditions: SOCl2
What Happens: Converts carboxylic acid to acyl chloride
Alternatives: PCl5
Functional Group: Carboxylic Acid
Reaction Conditions: HA (Acid) and 1° Alcohol
What Happens: Converts to an ester (or lactone)
Alternatives: N/A
Functional Group: Carboxylic Acid
Reaction Conditions: 1) NH3 ammonia + 2) Heat
What Happens: Converts to an amide + H2O
Alternatives: N/A
Functional Group: Carboxylic Acid
Reaction Conditions: Heat
What Happens: Decarboxylation - becomes R’ group and CO2
Alternatives: N/A
Functional Group: Acyl Chloride
Reaction Conditions: H2O
What Happens: Converts to carboxylic acid and HCl (hydrolysis)
Alternatives: N/A
Functional Group: Acyl Chloride
Reaction Conditions: Carboxylic acid anion (lost H)
What Happens: Converts to anhydride and Cl-
Alternatives: N/A
Functional Group: Acyl Chloride
Reaction Conditions: 1° Alcohol and pyridine
What Happens: Converts to an ester, Cl-, and pyr-H+
Alternatives: N/A
Functional Group: Acyl Chloride
Reaction Conditions: R’NHR’’
What Happens: Converts to an amide, R’NHR’‘Cl
Alternatives: R’ or R’’ may be H
Functional Group: Acyl Chloride
Reaction Conditions: Benzene, AlCl3
What Happens: Conversion to ketones (Friedel-Crafts Acylation)
Alternatives: N/A
Functional Group: Acyl Chloride
Reaction Conditions: 1) LiAlH(t-BuO)3, 2) H3O+
What Happens: Converts to an aldehyde
Alternatives: N/A
Functional Group: Acid Anhydride
Reaction Conditions: H2O
What Happens: Hydrolysis - Conversion to 2 Carboxylic acids
Alternatives: N/A
Functional Group: Acid Anhydride
Reaction Conditions: 1° Alcohol (R’OH)
What Happens: Conversion to an ester and carboxylic acid
Alternatives: N/A
Functional Group: Acid Anhydride
Reaction Conditions: R’NHR’’
What Happens: Conversion to an amide and carboxylic acid
Alternatives: R’ or R’’ may be H
Functional Group: Acid Anhydride
Reaction Conditions: Benzene, AlCl3
What Happens: Conversion to an aryl ketone, carboxylic acid (Friedel-Crafts acylation)
Alternatives: N/A
Functional Group: Esters
Reaction Conditions: H2O, HA
What Happens: Hydrolysis - creates craboxylic acid and 1° alcohol
Alternatives: also use OH-, H2O (base catalyzed)
Functional Group: Esters
Reaction Conditions: 1° Alcohol with R’’ group
What Happens: Conversion to other esters (transesterification) and R’OH 1° Alcohol
Alternatives: N/A
Functional Group: Esters
Reaction Conditions: R’‘NHR’’’
What Happens: Conversion to amides and 1° Alcohol
Alternatives: R’’ or R’’’ may be H
Functional Group: Esters
Reaction Conditions: 2 R’‘MgX, Et2O, H3O+
What Happens: Reaction with Grignard Reagents, ends in 3° Alcohol w/ R, R’, R’’ groups
Alternatives: N/A
Functional Group: Esters
Reaction Conditions: 1)LiAlH4, 2)H3O+
What Happens: Reduction to 1° Alcohol, R-CH2OH
Alternatives: N/A
Functional Group: Amides
Reaction Conditions: H3O+, H2O
What Happens: Hydrolysis, makes carboxylic acid and lesser substituted amide
Alternatives: use OH- and H2O, makes carboxylic acid anion and a monosubstituted amide. R’, R’’, or R may be H
Functional Group: Amides
Reaction Conditions: P4H10, heat (-H2O)
What Happens: Dehydration, formation of nitriles
Alternatives: N/A
Functional Group: Nitriles
Reaction Conditions: H3O+
What Happens: Hydrolysis to carboxylic acid
Alternatives: H2O, OH- makes carboxylate anion
Functional Group: Nitriles
Reaction Conditions: 1) DIBAL-H, 2) H2O
What Happens: Reduction to an aldehyde
Alternatives: N/A
Functional Group: Nitriles
Reaction Conditions: 1) R’MgX, 2) H3O+
What Happens: Conversion to a ketone by Grignard reagent or organolithium reagent
Alternatives: R’Li instead of R’MgX
