Organic Chemistry 8: Carboxylic Acids (9-Carboxylic Acid Derivatives)

[...] functional groups contain a carbonyl and a hydroxyl group connected to the same carbon

carboxylic acid

• they are always terminal groups

Carboxylic acids use the suffix [...]

-oic acid

• salts are named with the suffix -oate

Carboxylic acids have a high boiling point due to [...]

hydrogen bonding

• they often as dimers in solution due to the hydrogen bonding

the acidity of a carboxylic acid can be enhanced by substituents that are electron-[withdrawing or donating]

withdrawing

The acidity of a carboxylic acid can be decreased by substituents that are electron-[withdrawing or donating]

donating

Identify the acidic proton

Identify the most acidic proton

this is a  β-dicarboxylic acid

Carboxylic acids can be made by the [...] of 1° alcohols or aldehydes

oxidation

KMnO₄

Na₂Cr₂O₇

K₂Cr₂O₇

CrO₃

The above list shows [oxidizing or reducing] agents that can form [...]

oxidizing agents that can form carboxylic acid

• PCC is weak and stops oxidizing at he aldehyde

Identify the functional group in red

• acyl groups are derived by the removal of one or more hydroxyl groups form an oxyacid (acid that contains oxygen)

In nucleophilic acyl substitution a [...] displaces the [...]

nucleophile displaces the leaving group

• the nucleophile attacks the electrophile carbonyl carbon, opening the carbonyl and forming a tetrahedral intermediate

• the carbonyl reforms kicking off the leaving group

The nitrogen containing functional group shown above is called a/an …

amide

• amides are synthesized from a carboxylic acid by replacing the -OH group with amino group that may or may not be substituted

Amides are given the suffix [...]

-amide

Amides are derivatives of carboxylic acids in which the [...] group has been replaced by a/an [...]

amine or ammonia

A/an [...] is a carboxylic acid derivative where –OH is replaced with -OR

ester

Esters are given the suffix [...]

-oate

Carboxylic acid can act as a nucleophile and attack a second carboxylic acid to form a/an [...]

anhydride

Both linear and cyclic anhydrides are given the suffix [...]

anhydride

A carboxylic acid can be reduced to a 1° alcohol with a strong reducing agent like [...]

LiAlH4

• NaBH4 is not strong enough to reduce a carboxylic acid

[...] is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO₂)

decarboxylation

• the reaction proceeds spontaneously when heated

[...] is an ester hydrolysis of triacylglycerols using a strong base like sodium or KOH

saponification

• they organize in water to form micelles

A/an [...] dissolves nonpolar organic molecules in its interior, and can be solvated with water due to its exterior shell of hydrophilic groups

micelle

The reagents used in acid halide synthesis are [...] and [...]

SOcl2 and PBr3

example of

-fischer esterification

• treatment of a carboxylic acid with an alcoholic in the presence of an acid catalyst leads to the formation of ester, along with the elimination H2O

Acid chloride

Amides

Anhydrides

Carboxylate

Esters

Place the above molecules in order from most reactive to least reactive in nucleophilic substitution reactions

Acid chloride > Anhydrides > Esters > Amides > Carboxylate

 

...] describes when a reaction cannot proceed (or significantly slows) because substituents crowd the reactive site

steric hindrance

[...] refers to uneven distribution of charge across a σ bond because of differences in electronegativity

induction

• the more electronegative group a carbonyl-containing compound has, the greater its reactivity

Increased ring strain in a molecule can make it [more or less] reactive

• ring strain

• more

[...] is the process of exchanging the R″ group of an ester with the R′ group of an alcohol

transesterification

• transformation of an ester

• alcohol is the attacking nucleophile

When a phosphodiester bond is formed, a/an [...] is released

pyrophosphate (ppi)

• the pyrophosphate can then be hydrolyzed into two inorganic phosphates (Pi)

This is the [keto or enol] form of acetone

enol

• enol form contains an alcohol

• keto form has a regular ketone or an aldehyde