Organic Chemistry: Chapter 8

Front 1

How are cyclic carboxylic acids named?

Back 1

Cyclic carboxylic acids are named by listing the cycloalkane with the suffix carboxylic acid.

Front 2

How are salts of carboxylic acids named?

Back 2

Carboxylic acids salts are named with the siffix -oate instead of -oic acid.

Front 3

What is a dimer?

Back 3

A dimer is a connection or pairing between two molecules connected by hydrogen bonds.

Front 4

Sunstituents on carbon atoms near a carboxyl group influence anion stability and therefore effect acidity. What are some groups that stabalize the anion(electron withdrawing groups)? What are some destabalizers (electron donating groups)?

Back 4

Groups like NO2 or halides act as electron withdrawing groups working to stabalize the anion and increasing acidity. Donating groups like NH2 or OCH3 destabalize.

Front 5

Whats dynamic about the acidity in dicarboxylics acids?

Back 5

As dicarboxylic acids have 2 carbonyl groups, there are more profound indictive effects. This creates an extremely acidic alpha hydrogen. Interestingly enough, the other non cleaved hydrogen of the other carboxylic acid will be more difficult to deprotonate as this would create a species that is doubly-negatively charged.

Front 6

Can secondary and tertiary alcohols be oxidized into carboxylic acids?

Back 6

No! Only primary alcohols can be oxidized into carboxylic acids.

Front 7

Many reactions in which carboxylic acids and their derivatives proceed via a single mechanism. This is nucleophilic acyl substitution. What is nucleophilic acyl substitution?

Back 7

Nucleophilic acyl substitution occurs when a nucleophile molecule replaces the leaving group of an acyl derivative.

Front 8

What are cyclic amides named? How do we name them for IUPAC purposes?

Back 8

Cyclic amides are known as lactams. They are named by replacing -oic acid with -lactam.

Front 9

Do condensation reactions afford wayer or consume it?

Back 9

In a condensation reaction, water is a product.

Front 10

Explain the process of esterification when reacting varboxylic acids with alcohols under acidic conditions.

Back 10

Esterificarion is a condensation reaction. The carbonyl oxygen can become protonated, which enhances the polarity of the bond.

Front 11

How do we name cyclic esters?

Back 11

Cyclic esters are named using the suffix -lactone, which replaces -oic acid.

Front 12

These species are formed by the condensation of two carboxylic acids.

Back 12

These species are known as anhydrides.

Front 13

What types of agents can reduce a carboxylic acid to an aldehyde, then be further reduced to an alcohol?

Back 13

Carboxylic acids need a steon reducing agent such as LiAlH4. Reducing agents such as NaBH4 are not stron enough to reduce carboxylic acids.

Front 14

What does decarboxylation result in?

Back 14

Decarboxylation results in the forming of an enol, which then stabalizes into the keto form. As a consequence, CO2 is a product of the reaction.

Front 15

We know that decarboxylation occurs spontaneously under heat, but what is necessary for the parent molecule to actually undergo decarboxylation?

Back 15

Decarboxylation occurs in 1,3-dicarboxylic acids an other B-keto acids. This form is necessary as it promotes a stable, cyclic transition state that permits simaltaneous hydrogen transfer as well as loss of CO2

Front 16

What conditions are nucleophilic acyl substitution supported in?

Back 16

Nucleophilic acyl substitution occurs in both acidic and basic conditions. Basic conditions make the nucleophile more nucleophilic, and acidic conditions make the electrophile more electrophilic.