MCAT Chemical Processes: Ald, Ket, Phenols, Carboxylic Acids and Derivatives

alkyl

boiling point order

ketones

are aldehydes or ketones more stable?

hydrate formation

When an aldehyde or ketone is treated with water, the carbonyl group can be converted into this

under basic conditions

acetal formation

In acidic conditions, an aldehyde or ketone will react with two molecules of alcohol to form a....

Common acids used for this purpose include para-toluenesulfonic acid(TsOH) and sulfuric acid(H2SO4) (2nd example in image)

hemiacetal

final product in ald/ket + alcohol and alkoxide reaction (can only be treated one time)

thioacetal

2 Sulfide linkages in place of aldehyde used for protection

acetal protecting group

used when want to target reduction of carboxylic acid but also have a ketone/aldehyde attached

protects ket/ald while strong base reduces carboxylic acid

water then hydrolyzes this group

imine

A double bond between a carbon and a nitrogen

enamine

An amino group attached to a carbon that is double-bonded to another carbon.

primary amine

NH2

secondary amine

R2NH

imine

ketone + primary amine

catalyzed by H2SO4

enamine

ketone + secondary amine

catalyzed by H2SO4

oxime

hydrazone

ketone + primary amine

imine + H20/H+

oxime

ketone + NH2-OH, H+

hydrazone

ketone + NH2-NH2 + H+

secondary alcohol

aldehyde with GR and water

tertiary alcohol

ketone with GR and water

primary alcohol

aldehyde with NaBH4 and water/alcohol

secondary alcohol

ketone + NaBH4 and water/alcohol

primary alcohol

aldehyde with LAH and water

NaBH4

can reduce aldehydes and ketones

LAH

can reduce aldehydes, ketones, esters and carboxylic acids

carboxylic acid

aldehyde + tollen's reagent

ketone

secondary alcohol + tollen's reagent

aldehyde

primary alcohol + PCC

ketone

secondary alcohol + Jones Reagent/PCC

no reaction

tertiary alcohol + Jones Reagent

carboxylic acid

primary alcohol + Jones Reagent

protection of alcohols

--the best protecting group for alcohol is the trimethylsilyl group.

-to protect, add Cl-SiMe3 to R-OH.

-the alcohol gets "capped" into R-O-SiMe3

-to deprotect, add F-.

mesylate

*contain functional group -SO3CH3

-derived from methanesulfonic acid

-prepared using methylsulfonyl chloride and an alcohol in presence of a base

-serve as protecting groups when we don't want alcohols to react

-will not react with many of the other reagents that would attack alcohols

tosylate

*contain functional group -SO3C6H4CH3

-derived from toluenesulfonic acid

-can serve as protecting groups when we don't want alcohols to react

-will not react with many of the other reagents that would attack alcohols

SN1

The formation of a carbocation and leaving group followed by a nucleophilic attack is a description of the steps of a/n ___ reaction.

SN2

requires a strong nucleophile, adds antiperiplanar switching stereochemistry

aromatic

ring with continuously overlapping planar p orbitals

4n+2 pi electrons in ring

acid chloride

A carboxylic acid added with SOCl(2) will form what type of molecule?

ester

an organic compound made by chemically combining an alcohol and a carboxylic acid acid

thioester

combine carboxylic acid with a thiol (R-SH)

acid anhydride

carboxylic acid + acid chloride and strong base

amide

carboxylic acid + amine

reactivity order

1. acid chloride

2. acid anhydride

3. thioester

4. ester

5. amide

6. carboxylate ion

primary alcohol

carboxylic acid + LAH or BH3/THF

decarboxylation

double carboxylic acid + heat forms carboxylic acid + CO2

alpha substitution

c acid + Br2/PBr3 forms carboxylic acid + Br on alpha carbon and 2HBr