Organic Chemistry Exam 4

two aldehydes

dial

2 benzene rings fused together

naphthalene

aromatic ring with aldehyde

carbaldehyde

HCHO

Formaldehyde (or methanal)

CH3CHO

acetaldehyde (or ethanal)

H2C=CHCHO

Acrolein (or propenal)

CH3CH=CHCHO

Crotonaldehyde (or 2-Butenal)

benzene ring with aldehyde

Benzaldehyde

two ketones

dione

acetone

acetophenone

benzophenone

when there is bro an aldehyde and ketone present

• name as aldehyde at end

• name location of ketone as oxo

• ex. 3-Oxohexanal

ketones can’t be ___?

oxidized

• unless there are hot conditions

aldehydes will react faster than ketones because

they are less stable due to less hinderance and because they have less electronic support

geminal

both OH on the same carbon

hydration of aldehyde and ketones creates..?

geminal diols

nucleophilic addition of primary amine creates

• imine

• schiff base

nucleophilic addition of secondary amine creates

enamine

imine

enamine

schiff base

• created by the nucleophilic addition of primary amines

• carbon nitrogen double bond

N,N-dimethyl amine

Wolff-Kishner Reaction

• reagent is hydrazine

• turns C=O to H-C-H

• getting rid of carbonyl

Hydrazine

H2NNH2

acetal

• 2 O-R

• used to protect carbonyls

ylide

phosphorus with 3 H

Gilman Reagent

• R₂CuLi

• only uses one R group

2 carboxylic acid groups

dioic acid

carboxylic acid has the ____ naming priority in functional groups

highest

HCO2H

formic acid

CH3CO2H

acetic acid

CH3CH2CO2H

propionic acid

HO2CCO2H

Oxalic acid

naming nitriles

leave e in

acetonitrile

acetic acid + nitrile (CH3CN)

benzene ring + nitrile

benzonitrile

aromatic ring + nitrile

carbonitrile

cyano

when there is another carboxylic acid derivate present with nitrile

dimer

2 carboxylic acid molecules together

the acidic strength of ethanol is ____ than carboxylic acid

weaker

why is acetic acid more stable than ethanol

because it is more acidic and because it has resonance

buffers

• resist PH change

• ex. blood

• weak acid with its conjugate base

• Henderson-Hasselbalch equation

substituent effect on acidity

easier to donate H if you increase electronegativity

The closer the Electron withdrawing group to carboxylic acid, the ___ the acid because hydrogen will feel it

stronger

What does the reagent PBr3 do

replaces OH with Br

Acid Halides

RCOX

Anhydrides

RCOOCR’

Esters

RCOOR’

Amides

RCONR’2

Thioesters

RCOSR’

naming carboxylic acid derivates

name as carboxylic acid first, then change the end

naming acid halides

• -ic acid → -yl chloride

• -oic acid → -oyl bromide

• cyclohexane carboxylic acid → cyclohexanecarbonyl chloride

Naming Acid Anhydride

• an=without, hydride= water

• ic acid → -ic anhydride

• oic acid → -oic anhydride

naming esters

• -ic acid → -ate

• -oic acid → -oate

• malonate → two esters

naming amides

• -ic acid and -oic acid → amide

• When R is connected to N, treat N like a number (ex. N-methylpropanamide)

Naming Thioesters

• don’t need to know much

• what ever is connected to S is the first name + thio bro tbh idek

reactivity of carboxylic acid derivates

more Hydrogens = more reactive/acidic

which carboxylic acid derivate is the least reactive

amides (1) and Esters (2)

which carboxylic acid derivates are the most reactives

Acid Anhydrides (2) and Acid Chloride (1)

hydrolysis

reaction with water to yield a carboxylic acid

Alcoholysis

reaction with an alcohol to yield an ester

Aminolysis

reaction with ammonia or an amine to yield an amide

Reduction

Reaction with a hydride reducing agent to yield an aldehyde or an alcohol

Grignard Reaction

reaction with an organometallic reagent to yield a ketone or an alcohol (with extra carbon)