Studied by 60 peopleester nomenclature
Esters are named as alkyl alkanoates. The alkyl group connected to the oxygen is named first, followed by the group attached to the carbonyl.
The acyl portion is named by substituting the suffix -ate
Amide nomenclature
When naming amides, replace the -ic acid or -oic acid of the corresponding carboxylic acid with -amide. Substituents, irrespective of whether they are attached to the acyl group or the amide nitrogen, are listed in alphabetical order. Substitution on nitrogen is indicated by the locant N-.
nitriles
substitutive IUPAC names for nitriles add the suffix -nitrile to the name of the parent hydrocarbon chain that includes the carbon of the cyano group
less stable to most stable
acyl chlorides, acid anhydrides , esters, amides
acyl chlorides to carboxylic acids
acyl chlorides to acid anhydrides
acyl chlorides to esters
acyl chlorides to amides
acid anhydrides to esters
acid anhydrides to amides
carboxylic acid to ester
Baeyer-Villiger oxidation of ketones
oxygen goes to the more substituted side
esters to amides
hydrolysis of esters
acid catalyzed hydrolysis of esters
saponification
RETENTION OF CONFIGURATION
Reaction of Esters with Grignard and Organolithium Reagents and Lithium Aluminum Hydride
Amide Hydrolysis
Formation of (+) tetrahedral intermediate and then disassociation of NH3
Amide Hydrolysis in Basic Solution
products are carboxylate and ammonia
Nucleophilic substitution by cyanide ion
Cyanohydrin formation
Nitrile Hydrolysis in Basic Solution
nitriles to ketones
Write the structure for this name
Write the structure for this name
What does this yield?
Mechanism of reaction between esters and amines
Claisen Condensation
ethyl phenylacetate
retrosynthesis of this compound
write the mechanism
diethyl malonate
make 2-Bromo-3-pentanone from 3-pentanone
make 1-Penten-3-one from 3-pentanone
make 3-Hexanone from 3-pentanone
make 2-Methyl-l-phenyl-l-penten-3-one from 3-pentanone
2-Allyl-1,3-propanediol from propene
3-Phenylpropanoic acid from benzyl bromide
and use PCC to make the alcohol to a aldehyde
Make the alcohol to an aldehyde. Diels Alder is last
Outline a reasonable mechanism
Outline a reasonable mechanism
First add the hydroxide, then reinstate the carbonyl by taking a hydrogen from water. Then the rest is the photo
Outline a reasonable mechanism
Enol
acid catalyzed
Enolate
Aldol condensation mechanism
aldol condensation trick
replace the alpha hydrogen with the double bond of the electrophilic carbonyl
state the product
a strong base used to create enolates
LDA
Claisen Condensation
one ester is the source of both the acyl group and the enolate and the product is a β-keto ester (must have at least 2 alpha hydrogens)
Claisen Condensation Mechanism
Alkylation of enolates
Simple aldehyde, ketone, and ester enolates are relatively basic, and their alkylation is limited to methyl and primary alkyl halides
Alkylation of bicarbonyls, hydrolysis and decarboxylation
Methyl, primary, and unhindered secondary alkyl halides are satisfactory alkylating agents. Elimination (E2) is the only reaction with tertiary alkyl halides
Acid catalyzed enolization mechanism
Halogenation of aldehydes and ketones
X2 and an acid (ie acetic acid)
Haloform reaction
Methyl ketones undergo a novel C–C cleavage on treatment with excess halogen in the presence of base.
Haloform Reaction Mechanism
Substitution of deuterium for hydrogen at the α-carbon atom of an aldehyde or a ketone is a convenient way to introduce an isotopic label into a molecule and is readily carried out by treating the carbonyl compound with deuterium oxide (D2O) and base
Which is more stable?
α,β-unsaturated aldehydes and ketones are more stable than their nonconjugated isomers
What is the product?
The Michael reaction is an alkylation in which unsaturated ketone serves the same kind of electrophilic role that alkyl halides do toward the enolate.
lithium dialkylcuprates and alpha-beta conjugated ketones
The beta carbon of an alpha, beta unsaturated carbonyl compound is electrophilic;
The nucleophile bonds to the beta carbon
Note
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