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Level 199

Aldehydes & Ketones: NucleopHilic Addition


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-al, -dial
What is the suffix of the compound when the longest continuous chain contains an aldehyde group? or two aldehyde groups?
carbaldehyde
When a formyl group is attached to a ring, what is ring name followed by?
aldehyde
A carbonyl group with one allkyl grp and one H
one
How many electrons does silver have to give up in order to achieve a pseudo-noble-gas electron configuration
ketone
A carbonyl grp with 2 alkyl groups attached
Yes, because aldehydes and ketones have higher dipole-dipole forces
Do aldehydes and ketones have higher boiling points than alkenes? Why?
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
Because they can hydrogen bond with water molecules.
Why are aldehydes and ketones more soluble in water than alkenes?
yes
Are alcohols more soluble in water than aldehydes and ketones?
1.O3, 2. H2O, Zn
What are the 3 reagents needed for the ozonolysis of alkenes?
What are the 2 reagents needed for hydration of alkynes?
Sulfuric acid, Mercury sulfate. (Make sure the alkyne is being added to water first)
Aromatic ring with a carbonyl-r group substituent and HCl
What are the products of reaction of aromatic ring with acyl chloride?
Aromatic ring with a carbonyl-R group substituent and carboxylic acid
What are the products of reaction of aromatic ring with acid anhydride?
PCC, PDC
What are the 2 gentle oxidizing agents used to synthesize aldehydes?
true
(ex mg)
To convert carbonyl groups to methylene units. Hydrazine(H2NNH2), KOH, Diethylene glycol, heat.
What is the purpose of the Wolff-Kishner reduction, and what are the reagents needed to carry it out?
Hydrogenation with metal catalyst; Using NaBH4 or LiAlH4.
Name 2 general methods to reduce a carbonyl group to an alcohol:
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.
Remove water (with benzene, etc)
How do you drive imine formation to completion?
Primary amine (RNH2)
Aldehyde/Ketone must be reacted with what kind of compound in order to produce an imine?
Enamine (alkenyl substituted amine)
Reaction of aldehyde/ketone with secondary amines produces what type of compound?
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)
H2NOH, H2NNHC6H5, H2NNHC=ONH2
What are the molecular formulas for the following: Hydroxylamine, Phenylhydrazine, Semicarbazide