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27 terms

Aldehydes and Ketones: Nucleophilic addition

Nucleophilic addition to the carbonyl group
STUDY
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What is the suffix of the compound when the longest continuous chain contains an aldehyde group? or two aldehyde groups?
-al, -dial
When a formyl group is attached to a ring, what is ring name followed by?
-carbaldehyde
What has higher priority, an aldehyde or an alcohol?
Aldehyde
What is the suffix of a compound characterized by a ketone?
-one
What has higher priority, aldehyde or ketone?
aldehyde
What has higher priority, ketone or alcohol?
ketone
Do aldehydes and ketones have higher boiling points than alkenes? Why?
Yes, because aldehydes and ketones have higher dipole-dipole forces
Compare the boiling points of alcohols, aldehydes, and ketones:
Aldehydes and ketones have lower boiling points than alcohols because they cannot form hydrogen bonds with each other
Why are aldehydes and ketones more soluble in water than alkenes?
Because they can hydrogen bond with water molecules.
Are alcohols more soluble in water than aldehydes and ketones?
yes
What are the 3 reagents needed for the ozonolysis of alkenes?
1.O3, 2. H2O, Zn
What are the 2 reagents needed for hydration of alkynes?
Sulfuric acid, Mercury sulfate. (Make sure the alkyne is being added to water first)
What are the products of reaction of aromatic ring with acyl chloride?
Aromatic ring with a carbonyl-r group substituent and HCl
What are the products of reaction of aromatic ring with acid anhydride?
Aromatic ring with a carbonyl-R group substituent and carboxylic acid
What are the 2 gentle oxidizing agents used to synthesize aldehydes?
PCC, PDC
True or false, chromium reagents are able to oxidize secondary alcohols.
True
What is the purpose of the Wolff-Kishner reduction, and what are the reagents needed to carry it out?
To convert carbonyl groups to methylene units. Hydrazine(H2NNH2), KOH, Diethylene glycol, heat.
Name 2 general methods to reduce a carbonyl group to an alcohol:
Hydrogenation with metal catalyst; Using NaBH4 or LiAlH4.
What has more effect on K of hydration, steric effects or electronic environment?
Electronic environment. The more the electrons are pulled away, the more exposed the carbonyl carbon is... and the more likely it is for the carbonyl to be hydrated.
What must be present for cyanohydrin formation to be carried out with an aldehyde or ketone?
HCN and a charged ion of -CN, such as KCN, NaCN, etc. Don't forget the acid workup of sulfuric acid needed to complete the cyanohydrin formation.
Which conditions favor acetal formation? Which favor acetal hydrolysis?
Excess alcohol favors acetal formation. Excess water favors acetal hydrolysis.
How do you drive imine formation to completion?
Remove water (with benzene, etc)
Aldehyde/Ketone must be reacted with what kind of compound in order to produce an imine?
Primary amine (RNH2)
Reaction of aldehyde/ketone with secondary amines produces what type of compound?
Enamine (alkenyl substituted amine)
What are ylides?
Neutral molecules that have 2 oppositely charged atoms, each with an octet of electrons, directly bonded to each other.
How do you retrosynthetically visualize the two reactants in a Wittig reaction?
Mentally cleave the C=C so that one carbon is derived from a carbonyl group, and the other is derived from an ylide. (Turn one carbon into a carbonyl carbon, and attach the other to triphenyl phosphorus)
What are the molecular formulas for the following: Hydroxylamine, Phenylhydrazine, Semicarbazide
H2NOH, H2NNHC6H5, H2NNHC=ONH2