orgo chem carboxylic acids and esters

How do we name the parent chain that has a carboxylic acid?

By using the suffix -oic acid

What is a dicarboxylic acid?

An acid that contains two carboxyl groups at each end of the parent chain

What are poly functional acids?

Acids that contain one or more additional functional groups besides the carboxyl group

Are carboxlyic acids the most polar or nonpolar compound?

Polar

How are carboxylic acids made?

By the oxidation of a primary alcohol and aldehyde

What is a carboxylate ion?

A negative ion produced when a carb acid loses one or more acidic hydrogen ions

How can the solubility of a carb acid be greatly increased?

By converting them to a carboxylic acid salt

Esters are derivatives of what? What do they replace?

Carboxylic acids. Esters replace the -OH in COOH with -OR, COOR.

The condensation reaction of a carb acid with an alcohol by using a strong acid is called what?

Esterification

Low molecular mass esters are soluble in water because?

Esters can hydrogen bond with water, so they are soluble as long as their molecular weight is small

What functional group is this?

Carboxyl group

Can carboxyl groups be a part of ring structures?

No, they can only be attached by way of making the ring structure a substituent. 

What functional group is this? Is this a carboxylic acid derivative?

Ester, yes it is

What functional group is this? Is this a carboxylic acid derivative?

Acid chloride, yes it is

What functional group is this? Is this a carboxylic acid derivative?

Acid anhydride, yes it is

What functional group is this? Is this a carboxylic acid derivative?

Amide, yes it is

What is the acyl group?

The portion of the molecule that remains when Z group has been removed

What does “Z” mean when it comes to acyl groups?

The Z group is the portion of molecule that describes the differences in molecules, such as in Carboxylic acids, the -OH is the Z group, in Esters the -OR is the Z group, in Acid chloride the -Cl is the Z group, etc…

What is the difference between carbonyl compounds and acyl compounds?

In a carbonyl compound, the carbon is attached to a hydrogen or another atom. In an acyl compound the carbon is attached to specifically an oxygen, nitrogen, or halogen group.

Which functional groups are carbonyl compounds?

aldehydes and ketones

Which functional groups are acyl groups?

carboxylic acids and their derivatives 

For common name, what suffix do we use when naming a carboxylic acid with one carbon?

-form

For common name, what suffix do we use when naming a carboxylic acid with two carbons?

-acet

For common name, what suffix do we use when naming a carboxylic acid with three carbons?

-propion

For common name, what suffix do we use when naming a carboxylic acid with four carbons?

-butyr

For common name, what suffix do we use when naming a carboxylic acid with five carbons?

-valer

For common name, what suffix do we use when naming a carboxylic acid with six carbons?

-capro

For common name, what greek letter do we use for a carboxylic acid if a substituent is on the second carbon?

a

For common name, what greek letter do we use for a carboxylic acid if a substituent is on the third carbon?

B

For common name, what greek letter do we use for a carboxylic acid if a substituent is on the fourth carbon?

y

For common name, what greek letter do we use for a carboxylic acid if a substituent is on the fifth carbon?

S

What is the pneumonic for common name prefixes for carboxylic acids?

Frogs are polite, being very courteous (Formic, acet, propin, butyr, valeric, capro)

For common name, what suffix do we use when naming a dicarboxylic acid with two carbons?

oxal-

For common name, what suffix do we use when naming a dicarboxylic acid with three carbons?

malon-

For common name, what suffix do we use when naming a dicarboxylic acid with four carbons?

-succin

For common name, what suffix do we use when naming a dicarboxylic acid with five carbons?

glutar-

For common name, what suffix do we use when naming a dicarboxylic acid with six carbons?

adip-

For common name, what suffix do we use when naming a dicarboxylic acid with seven carbons?

pimel-

Do we also use greek letters when using common name for dicarboxylic acids?

Yes

Is there a dicarboxylic acid that has one carbon?

No there isn’t

What is the pneumonic for dicarboxylic acids?

Oh my, such good apple pie (Oxal, malonic, succin, glutar, adip, pimel-)

What is an unsaturated acid?

A polyfunctional acid that contains a double bond and has a wide variety of uses

What is a hydroxy acid?

An acid that contains a hydroxyl group

What is a keto acid?

Acid that has a ketone and carboxyl group

Carboxylic acids are soluble when they have how many carbons?

Less than five

Carboxylic acids boiling point increases as?

The number of carbons increase

What is the tier list of compounds when it comes to boiling point? (highest to lowest)

Acids → alcohol → aldehydes → alkanes

Can carboxylic acids hydrogen bond to themselves?

Yes 

Ionization

Occurs in aqueous solution, acid → carboxylate ion (COO-)+ H3O+

neutralization

reaction with a base (NaOH), acid → carboxylate salt (CONa+) + H2O

decarboxylation

A carbon dioxide molecule is produced, acid → CO2 + smaller organic molecule

Is a carboxylate ion a weak or strong acid?

Weak acid

How do we name a carboxylate ion?

-ic acid turns into -ate

How do we name an ester?

Name the alkyl part first (the group extending from the second O) and then name the acyl group, finally add the suffix -oate

What makes the smell/odor of raspberry?

Isobutyl methanoate - R/IBM

What makes the smell/odor of pear?

Propyl ethanoate - P/PE

What makes the smell/odor of banana

Pentyl ethanoate - B/PE

What makes the smell/odor of orange?

octyl ethanoate - O/OE

What makes the smell/odor of apricot?

pentyl propionate - A/PP

What makes the smell/odor of apple?

methyl butanoate - A/MB

What makes the smell/odor of pineapple?

ethyl butanoate - P/EB

What else do esters make? 

pheromones 

What is the alarm pheromone in bees?

Isoamyl acetate AB/ISA

What are commonly used esters?

Benzocaine - used as a local anesthesia

Aspirin - used as an analgesic

Oil of wintergreen - used in rubs and creams for muscle soreness

Can esters hydrogen bond in water?

Yes

Can esters hydrogen bond to themselves?

No

What is the solubility limit of esters?

The solubility limit is fewer than 5 carbons

Esters are completely soluble with how many carbons?

1-2 carbons

Esters are slightly soluble with how many carbons?

3-5 carbons 

Is an esters boiling point higher or lower compared to aldehyde or alcohol with a similar number of carbons?

Lower 

What is the tier list of boiling point based on lowest to highest?

Ether, ester, aldehyde, alcohol, acid

What is the reverse reaction of condensation? What products are made? Is a strong acid or base used?

Acidic hydrolysis, COOR + H2O → COOH + R-OH, a strong acid 

What is hydrolysis of an ester under basic conditions, and what product is made?

Ester saponification, COOR + NaOH (strong base) → COONa+ (carboxylate salt) + R-OH