Reading...
Play button
Play button
Use LEFT and RIGHT arrow keys to navigate between flashcards;
Use UP and DOWN arrow keys to flip the card;
H to show hint;
A reads text to speech;
41 Cards in this Set
- Front
- Back
|
Are imides or amides more acidic? Why?
|
Imides are more acidic, because the resulting negative charge is destabilized by the carbonyl oxygens.
|
|
|
Acid Halide (CA derivative)
+ Water |
Carboxylic Acid,
It's called Hydrolysis |
|
|
Hydrolysis of An Acid Anhydride
|
Two Carboxylic Acids
|
|
|
Hydrolysis of an Ester
|
Requires Acid or Base (Remember Soponification?)
Results in a Carboxylic Acid and an Alcohol. |
|
|
Hydrolysis of an Amide
|
Acid or Base needed along with heat. Results in a Carboxylic Acid and the Ammonium Ion of the Amide leaving group.
|
|
|
Hydrolysis of a Nitrile
|
Needs heat and a strong acid. Notice that the first step forms an amide, and then it continues to form a Carboxylic Acid.
|
|
|
Acid Chloride +Alcohol
|
Ester
|
|
|
Acid Anhydride + Alcohol
|
One Ester and one Carboxylic Acid
|
|
|
Ester +Alcohol
|
Transesterification, needs acid catalyst and excess alcohol
|
|
|
Amide + Alcohol
|
NO!
|
|
|
Nitrile + Alcohol
|
Nope
|
|
|
Acid Chloride + Amine
|
Amide, need 2 moles of Amine to neutralize the HCl byproduct
|
|
|
Acid Anhydride + Amine
|
Amide, need two moles of Amine to neutralize the acid byproduct.
|
|
|
Ester + Amine
|
Amide and an Alcohol(formed from leaving ester group)
|
|
|
Acid Chloride + Carboxylic Acid Salt
|
Acid Anhydride, good way to generate non-symmetrical acid anhydride
|
|
|
Ester + Grignard Reagent
|
Usually a tertiary alcohol, a secondary alcohol if you had an H on the carbonyl.
|
|
|
Acid Chloride + Lithium Diorganocuprate
|
Ketone
|
|
|
Ester + Lithium Aluminum Hydride
|
Two alcohols
|
|
|
Ester + DIBALH @ low temp.
|
Aldehyde and an alcohol
|
|
|
Amide + Lithium Aluminum Hydride
|
Amine Remember that the mechanism is interesting
|
|
|
Nitrile + Lithium Hydride
|
primary amine
|
|
|
2 Aldols + NaOH
|
beta-hydroxy aldehyde or ketone
|
|
|
beta-hydroxy ketone/aldehyde + acid or base
|
dehydration- forms C=C bond and ejects water
|
|
|
Ester + appropriate base, followed by water and HCl
|
beta-ketoester
|
|
|
What is a Dieckman Condensation?
|
an intramolecular claisen condensation
|
|
|
Enamine + primary alkyl halide, followed by water and acid
|
ketone with whatever you attached.
|
|
|
Enamine + Acid Chloride, followed by water and acid
|
beta-ketone
|
|
|
Secondary Amine + Aldehyde or Ketone
|
Enamine
|
|
|
Sequence of Acetoacetic Ester Synthesis (example)
|
1. EtO- Na+
2. Primary Halide 3. NaOH, H2O 4. HCl, H2O 5. heat |
|
|
Malonic Ester Synthesis
|
Same as Acetoacetic ester Synthesis, except there is a Ester (CA derivative) on both ends of the compound. Results in a carboxylic acid
|
|
|
Imagine in your head what happens when you add another EtO- and Primary Halide after the first two steps of Acetoacetic Ester synthesis
|
You can do it.
|
|
|
Acid Anhydride+ conjugated double bond with carbonyl group
|
Ketone with whatever your acid anhyrdide looked like.
|
|
|
Robinson Anucleation
|
Micheal Addition followed by Aldol Reaction. If you don't remember what these are put this one back.
|
|
|
beta- unsaturated ketone or Aldehyde + lithium diorganocuprate
|
conjugate addition to the double bond.
|
|
|
Imagine in your head what happens when you add another EtO- and Primary Halide after the first two steps of Acetoacetic Ester synthesis
|
You can do it.
|
|
|
Acid Anhydride+ conjugated double bond with carbonyl group
|
Ketone with whatever your acid anhyrdide looked like.
|
|
|
Robinson Anucleation
|
Micheal Addition followed by Aldol Reaction. If you don't remember what these are put this one back.
|
|
|
beta- unsaturated ketone or Aldehyde + lithium diorganocuprate
|
conjugate addition to the double bond.
|
|
|
Chromic Acid?
|
1. Create a Carboxylic Acid from a primary Alcohol
2. Create a ketone from a secondary alcohol! |
|
|
Protect a carbonyl!
|
Add a diol
|
|
|
Protect an alcohol!
|
Add a cyclic ether
|
