Organic Nucleophilic Substitution at Carbonyl Groups

What happens during nucleophilic substitution at carbonyl groups

carbonyl group is polarized (partially positive carbon) so nucleophiles bond as they would in addition, but a strong leaving group transforms the tetrahedral intermediate into a carbonyl again

identify the mechanism

nucleophilic substitution at carbonyl

identify the mechanism

acid catalyzed protonation of carbonyl oxygen

Under acidic conditions what will increase the tendency of a deconstruction of a tetrahedral intermediate with a poor leaving group

protonation of the LG

acid catalyzed nucleophilic substitution at the carbonyl will have a BLANK in the intermediate, non acid catalyzed will have a BLANK in the intermediate

protonated oxygen, negatively charged oxygen

What is the order of reactivity with carboxylic acids of esters, amides, acyl halides, and acid anhydrides

acyl chloride > acid anhydride > ester > amide

transesterification requires what reagents

ROK, ROH (where R is the final carbon chain/substituent of the product)

If an aldehyde is produced as an intermediate in nucleophilic substitution at carbonyl carbon, what will occur when there is no good leacing group present

it will be reduced to a primary alcohol

If a ketone is produced as an intermediate in nucleophilic substitution at carbonyl carbon, what will occur when there is no good leacing group present

it will be reduced to a secondary alcohol

what is produced in the reaction of esters with grignard reagents and organolithium reagents

tertiary alcohol with two identical alkyl groups attached to the carbon atom bearing the hydroxyl group

Organocuprate reagents are necessary for the production of a ketone from BLANK because BLANK

esters, they only react with alkyl halides

the transformation of an acyl halide to a ketone required what kind of reagent

organometallic

If the final desired product is a ketone from an alkyl halide, what reagent will prevent the formation of a tertiary alcohol

lithium dialkylcuprates

Acyl chlorides will transform into an ester with what reagent

alcohols/ weak base

Identify the mechanism

acid catalyzed ester hydrolysis

Identify the mechanism

base catalyzed ester hydrolysis