Module 9: Carboxylic Acids

Carboxylic acids take their names from the alkane that contains the same number of carbons as the longest continuous chain that contains the _____. The

-e ending is replaced by -oic acid. Numbering begins at the carbon of the ____ gorup.

COOH, COOH

What is the name of this molecule?

pentanoic acid

What is the name of this molecule?

3-methylpentanoic acid

What are the systematic and common names for this molecule?

Systematic: methanoic acid

common: formic acid

what are the systematic and common names of this molecule?

systematic: ethanoic acid

common name: acetic acid, also written as CH3COOH

what are the systematic and common names of this molecule? also written as CH3C(OH)HCO2H

systematic: 2-Hydroxypropanoic acid

common: lactic acid

what are the systematic and common names of this molecule?

systematic: Benzenecarboxylic acid

common: Benzoic acid

what are the systematic and common names of this molecule?

systematic: o-Hydroxybenzenecarboxylic acid

common: Salicylic acid

what are the systematic and common names of this molecule? also written as HO₂CCH₂CO₂H

systematic: propanedioic acid

common: Malonic acid

what are the systematic and common names of this molecule? also written as HO₂CCH₂CH₂CO₂H

systematic: butanedioic acid

common: succinic acid

what are the systematic and common names of this molecule?

systematic: 1,2-Benzenedicarboxylic acid

common: Pthalic acid

The carbon of a carboxylic acid group has what kind of geometry? what is the hydridization of the carbon?

trigonal planar, Csp²

- Carboxylic acids have higher boiling and melting points than alcohols due to ____.

- more hydrogen bonding = ____ melting/boiling points.

- Carboxylic acids are more acidic than _____.

- higher electronegativity = more ____ effect = more ___

- more electron withdrawing groups are favored to increase ____

hydrogen bonding

higher

alcohols

inductive, acidity

acidity

Carboxylic acids are more acidic than alcohols due to stabilization by _____.

resonance structures

more stable conjugate base means the base is ____ and more ___ meaning its conjugate acid is ____.

weaker, stable, stronger

The shorter the carbon chain, the ____ the acidity.

higher

rank these in terms of decreasing acidity

A > B > C > D, the opposite is true for hydrocarbons

Rank these in order of decreasing acidity

HI > HBr > HCl > HF, comparing by size and polarizability

Rank these in terms of decreasing acidity

A > B > C

Rank these in terms of decreasing acidity

A > B > C, the closer the electronegative element is, the more acidic the molecule will be

The more alkyl groups present, the _____ acidic the molecule will.

less

Rank these in terms of decreasing acidity.

B > A

To increase acidity of carboxylic acids, add more electron _____groups ____ to the CO₂H.

withdrawing, closer

to decrease acidity, add more electron _____ groups ____ to the carboxylic group.

donating, closer

alkyl groups are electron ____ groups and make carboxylic acids ___ acidic.

donating, less

rank these in terms of decreasing acidity.

C > A > B