ultimate Ch. 20 study set

suffix for monocarboxylic acids

oic acid

What is the suffix for when carboxylic acid is connected to a ring?

carboxylic acid

What locant does the C atom of COOH take in a monocarboxylic acid?

1

Know the common IUPAC for monocarboxylic acids.

ok

suffix for diacids

dioic acid

Know the common IUPAC for diacids.

ok

What are deprotonated carboxylic acids?

carboxylate salts

suffix for carboxylate salts

ate

What hybridization are carboxylic acids?

sp3

What geometry are carboxylic acids?

trigonal planar

How many hydrogen bond interactions can COOH form?

2

What is the pKa of most COOH?

4-5

Is the boiling point of carboxylic acids high or low?

relatively high

What forms when COOH is treated with a strong base such as NaOH?

carboxylate salt

Does equilibrium favor carboxylic acid or carboxylate salt?

carboxylic acid

The acidity of carboxylate acid is primarily due to the stability of the_____ _____ which is stabilized how?

conjugate base stabilized by resonance

With the addition of electron-withdrawing substituents, does the pKa of COOH increase or decrease?

decrease

If the conjugate base of a carboxylic acid is resonance stabilized, does acidity increase or decrease?

increase

What is a common electron-withdrawing group that is not a halide?

nitro group NO2

What are the 4 common carboxylic acid derivatives?

acid halide, acid anhydride, ester, amide

What is the suffix for acid halides? Given acetic acid, what is the acid halide form using Br?

acetyl bromide

What is the suffix for an acid halide group connected to a ring? Given cyclohexanecarboxylic acid, what is the acid halide form using Cl?

Cyclohexane carbonyl chloride

What is the suffix for anhydrides? Given acetic acid, what is the anhydride form?

acetic anhydride

What is the suffix for esters? Give acetic acid, what is the ester form?

ethyl acetate

What is the suffix for esters connected to a ring? Given Cyclohexanecarboxylic acid, what is the ester form?

Methyl cyclohexanecarboxylate

What is the suffix for amides? Given acetic acid, what is the amide form?

acetamide

What is the IUPAC of this compound?

N-Methylacetamide

What is the IUPAC of this compound?

N,N-Dimethylacetamide

Which part of a carboxylic acid or derivative can act as a base/nucleophile?

the OH group

What is a Bronsted-Lowry acid?

any species that can donate a proton

True or False: carboxylic acids can act as Bronsted-Lowry acids.

True

How do you get pKa from Ka?

-log(Ka)

How do you get Ka from pKa?

10^(-pKa)

Rank the reactivity of the 4 common COOH derivatives from least to most reactive:

Amides < Esters < Anhydrides < Acid halides

Do carboxylic acids or carboxylate ions dominate when pH < pKa?

carboxylic acids

Do carboxylic acids or carboxylate ions dominate when pH > pKa?

carboxylate ions

Generally, are carboxylic acids or carboxylate ions more soluble in water? Why?

carboxylate ions because of their charge

Water solubility of carboxylic acids can be increased when they are _____?

ionized

There are 3 oxidation reactions that form carboxylic acids. What are the oxidated reactants in ABC order?

alkylbenzenes, alkynes, primary alcohols

What is the oxidation reagent for alkylbenzenes and primary alcohols to form carboxylic acids?

Na2Cr2O7/H2SO4, H2O

Which reactant undergoes oxidation reaction to form a carboxylic acid via an oxidative cleavage?

alkynes

What are the reagents for oxidative cleavage of alkynes to form carboxylic acids?

1. O3

2. H2O

What is the product when a Grignard reagent is treated with 1. CO2 / 2. H3O+?

carboxylic acid

What are the reagents to treat a Grignard reagent to make carboxylic acids?

1. CO2

2. H3O+

What is the product when nitriles are treated with H3O+ and heat?

carboxylic acids

What are the reagents to treat nitriles to form carboxylic acids?

H3O+ and heat

What is the product when nitriles are treated with OH-/H2O?