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110 Cards in this Set

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Aldehydes are named with suffix ___
-al
Aldehydes occupy what position?
the terminal position
Common names for the first five aldehydes are:
*formaldehyde
*acetaldehyde
propionaldehyde
butyraldehyde
valeraldehyde
t or f
A ketone can be a terminal functional group
f
it can NEVER be a terminal functional group
If the aldehyde is attached to a ring, we use the suffix ___
carbaldehyde
We name an aldehyde as a substituent with the prefix -formly if....
the aldehyde does not hold priority in the molecule
Ketones are named with the suffix ___
-one
When ketones are named as a substituent we use the prefix __.
-oxo
Physical properties of aldehydes and ketones are goverened by the presence of...
the carbonyl group
The dipole of a carbonyl is ___ than the dipole of an alcohol because the carbonyl lacks a ____.
greater, hydrogen
The B.P. of aldehydes and ketones is ___ than that in alcohols because....
less, because no hydrogen bonding is involved
aldehydes or ketones
Which is more reactive towards nucleophiles
aldehydes
An aldehyde can be obtained from the ___ of a ____.
partial oxidation, primary alcohol
A ketone can be obtained from the ____ of a ____.
oxidation, secondary alcohol
The only reagent that can oxidize a primary alcohol to and aldehyde is ___.
PCC
What is PCC?
A dry, nonhydrating oxidizing reagent
Oxidizing reagents for ketones include....
Sodium or potassium dichromate
chromium trioxide
PCC
What is Jones Reagent?
Chromium trioxide
t or f
Can double bonds be cleaved to form aldehydes and ketones?
t
Define Ozonolysis?
Breaks down double bonds using ozone
What does Friedel-Crafts Acylation produce?
It produces aromatic ketones in the form of R-CO-Ar
Aldehydes and ketones exist in the ___ form.
keto (C=O)
Acidic are basic
alpha protons
acidic
Which two isomers can aldehyes and ketones exist in?
keto and enol
Define enol
unsaturated alcohol
ene= double bond
ol= alcohol
Define tautomers
Two isomers which only differ in the placement of a proton
The equilibrium between the tautomrs lies far to the ___ side, so there will be more ___ isomers in solution.
keto, keto
Define enolization
the process of interconverting from the keto to the enol tautomer
Enols are important ___ in many reactions of aldehydes and ketones
intermediates
Tautomers are not resonance structures because...
they have different connectivity of atoms
ENOLIZATION AND REACTIONS OF ENOLS
The enolate carbanion acts as a ____.
nucleophile
ENOLIZATION AND REACTIONS OF ENOLS
The enolate carbanion can be created with a _____.
strong base
Strong bases include....
lithium diisopropyl amide (LDA)
Potassium hydride (KH)
ENOLIZATION AND REACTIONS OF ENOLS
A 1,3-dicarbonyl is extra acidic because...
there are 2 carbonyls to delocalize negative charge
ENOLIZATION AND REACTIONS OF ENOLS
Describe Michael additions
The nucleophilic carbanion reacts via SN2 with alkyl halides or α, β- unsaturated carbonyl compounds. The carbanion attaches to the unsaturated carbonyl at the β-position.
Aldehyde and ketone addition reaction trend: _____ addition to a ____!
nucleophilic, carbonyl
ADDITION REACTIONS
C=O is polarized with a partial ____ charge on C and a partial ___ charge on O.

This makes the carbon an ___.
positive, negative

electrophile
ADDITION REACTIONS
When a nucleophile attacks, it forms a ___ bond to the carbon, breaking the ___ bond in the C=O.
covalent, pi
ADDITION REACTIONS
The electrons from the pi bond are pushed on the ___, generating a ____.
oxygen atom, tetrahedral intermediate
ADDITION REACTIONS
if no good leaving group is present will the carbonyl re form?
no, the final product will be nearly identical to the intermediate
ADDITION REACTIONS
If a good leaving group is present what happens?
the carbonyl double bond can re-form and pulls off the leaving group
In the presence of water, ketones and aldehydes react to form ___.
gem-diols
HYDRATION REACTION
the ___ oxygen in water attacks the ____ carbonyl carbon
nucleophilic, electrophilic
The hydration reaction normally proceeds ____.
slowly
How can we increase hydration reaction rate?
Addition of acid or base
When one equivalent of alcohol is added to an aldehyde or ketone, the product is
a hemiacetal or hemiketal
We can always recognize a hemiacetal or hemiketal because..
it will still only contain one hydroxyl group
B/c the reaction with only one equiv. of -OH have proceeded 1/2way the product is termed...
In ___ the reaction would stop here
hemi, base
When 2 equiv. of -OH are added, the reaction proceeds all the way and the product is...
and acetal or ketal
B/c aldehydes contain a ___ on the carbonyl, both hemiacetals and acetals will still contain a ____ as a distinguishing characteristic.
hydrogen, hydrogen
Acetal and ketal formation reaction proceeds via the same mechanism as....
hydration
Acetal and ketal formation reactions are catalyzed by...
anhydrous acid
Acetals and ketals are comparatively ___, and used as ____ for carbonyl funtionalities
inert, protecting groups
What is a popular protecting group?
Ethylene glycol
What is ethylene glycol?
A diol and both alcohol groups come from the same molecule
Molecules with protecting groups can easily be converted back to carbonyls with _____ and ____.
aqueous acid and heat
Hydrogen cyanide is a classic ___.
nucleophile
Alkynes are fairly acidic b/c of...
their triple bonds
REACTIONS WITH HYDROGEN CYANIDE
after the ___ dissociates, the nucleophilic cyanide ____ can attack the carbonyl carbon atom.
hydrogen, anion
REACTIONS WITH HYDROGEN CYANIDE
Reactions with aldehydes and ketones produce stable compounds called
cyanohydrins
REACTIONS WITH HYDROGEN CYANIDE
The cyanohydrin gains its stability from the newly formed ____ bond.
C-C
REACTIONS WITH HYDROGEN CYANIDE
When a carbonyl reacts with HCl what happens?
A weak C-Cl bond is formed, and the resulting chlorohydrin isnt very stable
When you see a carbonyl carbon, think ____ first!!!
electrophile
Because they make good ___, ammonia derivatives react with carbonyls
nucleophiles
How are imines produced?
Ammonia adds to the carbon atom and water is lost
What is an imine?
Compound with a nitrogen atom double bonded to a carbon atom
A reaction in which water is lost between two atoms is termed...
condensation reaction
CONDENSATION WITH AMMONIA DERIVATIVES
The 1st part of the reaction follows ____ addition
nucleophilic
CONDENSATION WITH AMMONIA DERIVATIVES
Reactions forms ____ intermediate
tetrahedral
CONDENSATION WITH AMMONIA DERIVATIVES
A ___ bond forms b/w C and N and a leaving group (___) is kicked off.
double, water
CONDENSATION WITH AMMONIA DERIVATIVES
A leaving group is usually kicked off by the re-formation of the....
C=O bond
Common ammonia derivatives that react with aldehydes and ketones are:
H2NOH- forms oximes
H2NNH2- forms hydrazones
H2NNHCONH2- forms semicarbazones
Describe Adol Condensation.
An aldehyde acts both as an electrophile and a nucleophile
ADOL CONDENSATION
The enolate is more ____ than the enol because....
nucleophilic, negatively charged
ADOL CONDENSATION
The nucelophilic enolate ion can react with the carbonyl group of another ____ molecule
acetaldehyde
ADOL CONDENSATION
The product is ____, which contains both ____ and ____ functional groups
3-hydroxybutanal, alcohol and aldehyde
What is an adol?
Aldehyde + alcohol
ADOL CONDENSATION
With a ____ base and ___ temperatures condensation occurs
strong, high
ADOL CONDENSATION
We kick off a ___ molecule and form a double bond, producing an _____.
water, α,β- unsaturated aldehyde
ADOL CONDENSATION
The ____ acts as an electrophile, and the ____ acts as a nucleophile (in the form of an ___ ion)
carbonyl, aldehyde, enolate
The Witting reaction swaps out a __ for a ___.
C=O, C=C
The Witting reaction forms carbon-carbon double bonds by converting aldehydes and ketones into ____.
alkenes
WITTING REACTION
First step involves formation of a ___ from the SN2 reaction of an alky halide with the nucleophilic ____.
Phosphonium salt, triphenylphosphine
What is triphenylphosphine?
Phosphorous atom that has 3 aromatic phenyl groups attached to it
WITTING REACTION
The phosphonium salt is deprotonated with a ___ base, yielding a neutral compound called an ___ or ___.
strong, ylide or phsphorane
WITTING REACTION
The ylide form is a...
zwitterion
what is a zwitterion?
a molecule with both positive and negative charges
WITTING REACTION
The phosphorane form has ___ bond between ___ and ___.
double, carbon an phosphorus
WITTING REACTION
Is an ylide a type of carbanion?
yes
What kind of properties does an ylide have?
nucleophilic
WITTING REACTION
When combined with an aldehyde or ketone, and ylide attacks the carbonyl atom giving....
an intermediate called a betaine
WITTING REACTION
A betaine forms...
a four membered ring with an ionic bond b/w the oxygen and phosphorous
WITTING REACTION
What is an oxaphosphetane?
a ringed intermediate which decomposes to yield and alkene and triphenylphosphine oxide
Aldehydes are ___ oxidized than alcohols but ___ oxidized than carboxylic acids
more, less
Ketones are as oxidized as ___ carbons can get
secondary
Pretty much any oxidizing agent (except __) can oxidize aldehydes into ___.
PCC, carboxylic acids
Oxidizing agents include:
PCC, KMnO4, CrO3, Ag2O, and H2O2
The most common reagents used to reduce aldehydes and ketones to alcohols are...
LAH and NaBH4
What are 2 ways to reduce aldehydes and ketones all the way to alkanes?
Wolff-Kishner reduction
Clemmensen reduction
In the Wolff Kishner reduction, the carbonyl is first converted to ____
hydrazone
In the Wolff Kishner reduction hydrazone releases molecular ___ when it is heated with a ___, forming an ___
nitrogen, base (KOH), alkane
Wolff Kisher reaction is only useful when the product is __ under ___ conditions
stable, basic
In the Clemmensen reduction and aldehyde or ketone is heated with ___ in ___.
amalgamated zinc, HCl
What is ethylene glycol
a high boiling solvent
In a carbonyl, the carbon is ___ and the oxygen is ___.
positive, negative
Aldehydes can be synthesized from ____ with ___.
primary alcohols, PCC
Aldehydes can be oxidized to ___ or reduced to ____.
carboxylic acids, primary alcohols
Ketones cannot be further ___, but they can be reduced to ____.
oxidized, secondary alcohols
The enol form is significant because it can act as a ___, but is not prevalent in ____.
nucleophile, solution
Ammonia deriviatives often add in ___ reactions.
condensation