ALDEHYDES & KETONES Flashcards
Aside from Aldehydes & Ketones, what are the other carbonyl containing compounds?
Carboxylic acid and its derivatives
Have at least 1 hydrogen atom attached to the carbonyl carbon.
Aldehydes
Have 2 carbon groups attached to the carbonyl carbon.
Ketones
C=O is called
carbonyl carbon
C=O with R group is called
Acyl group
C=O with Hydrogen is called
Formyl group
Aldehyde group is synonymous with?
Formyl group
Acyl group found on Aldehydes/Ketones is?
Bonded to a hydrogen (aldehyde) or another carbon (ketone).
AND
it CAN’T stabilize negative charge
AND
it CAN’T act as a leaving group in a nucleophilic substitution reaction
Acyl group found on Carboxylic acid is?
Bonded to an atom (can be Oxygen, Halogen, Sulfur, Nitrogen).
AND
it CAN stabilize negative charge
AND
it CAN act as a leaving group in a nucleophilic substitution reaction
Bonded to a hydrogen (aldehyde) or another carbon (ketone).
Acyl group in Aldehydes & Ketones
it CAN’T stabilize negative charge
Acyl group in Aldehydes & Ketones
it CAN’T act as a leaving group in a nucleophilic substitution reaction
Acyl group in Aldehydes & Ketones
Bonded to an atom (can be Oxygen, Halogen, Sulfur, Nitrogen).
Acyl group in Carboxylic Acid & Its Derivatives
it CAN stabilize negative charge
Acyl group in Carboxylic Acid & Its Derivatives
it CAN act as a leaving group in a nucleophilic substitution reaction
Acyl group in Carboxylic Acid & Its Derivatives
Acyl group in carboxylic acid is bonded to an atom (can be ? ).
Oxygen, Halogen, Sulfur, Nitrogen
In nomenclature, carbon 1 would be the carbon with?
Carbonyl carbon
what suffix is added if the -CHO is attached to a cycloalkane
-carbaldehyde
what suffic is added if the -CHO is attached to a benzene ring
-benzenecarbaldehyde
Formaldehyde systematic name
Methanal
Acetaldehyde systematic name
Ethanal
Acrolein systematic name
Propenal
Crotonaldehyde systematic name
2-Butenal
Benzadehyde systematic name
Benzenecarbaldehyde
Propionaldehyde IUPAC name
Propanal
When is the prefix “oxo” used?
When ketone and aldehyde are NOT the functional groups; they become the substituent.
What functional group is higher than ketone and aldehyde?
Carboxylic acid and acid anhydride
Boiling point of Aldehydes & Ketones description?
Intermediate between alcohols and alkanes
Physical properties of aldehydes & ketones are due to the presence of?
Presence of carbonyl carbon (C=O)
carbonyl carbon (C=O) is polar or nonpolar?
Polar functional group
The boiling point increases with an increase in the size of the molecule so the chemical properties of Aldehydes & Ketones are due to the presence of a POLAR FUNCTIONAL GROUP or the CARBONYL CARBON.
Smaller compounds are soluble in water because?
They are Hydrogen bond acceptors.
The simplest aldehyde, is manufactured on a very large scale by the oxidation of methanol.
Formaldehyde
37% aqueous solution of Formaldehyde?
Formalin
It is a preservative and disinfectant; mostly used in the manufacture of plastics, building insulations, particle board and plywoods.
Formalin
It is a cold sterilant that is effective to kill microorganisms spores, resistant viruses used in proper concentration and even adequate contact time.
Formaldehyde
About half of acetaldehyde is produced anually to oxidize to?
Acetic acid
Manufactured mainly by the oxidation of ethylene over a palladium-copper catalyst.
Acetaldehyde
If ½ of acetaldehyde is used to oxidize acetic acid, the other ½ is used for?
Production of 1-butanol & other commercial chemicals.
The process of adding oxygen and removing hydrogen.
Oxidation
Boiling point of Acetaldehyde?
20°C , very close to room temp.
The source of Vanillin?
Vanilla bean
Aside from being a flavorant, aldehydes & ketones is also used in?
Perfumes
Introduced in 1921, and the first line fragrance to use synthetic organic chemicals. Also, the world’s 1st abstact fragrance & comprises more than 80 ingredients.
Chanel no. 5
What is the purpose of aldehyde in chanel no. 5?
To heighten the scents & give an airy nature to the floral notes.
Adjunct therapy in the symptomatic management of idiopathic Parkinson’s disease; also a Benzophenone.
Tolcapone
COMT meaning
catechol-O-methyltransferase
COMT inhibitor or catalyze/metabolyze active catechols.
Tolcapone
Primary treatment for Parkinson’s disease.
Levodopa/Carbidopa
Parkinson’s disease
tremor, rigidity, slowness of movement
Idiopathic meaning
cause is unknown
Opioid analgesic indicated for management of severe pain that is not responsive to alternative treatments.
Methadone
Synthetic opioid agonist for the management of chronic pain and for opioid dependence.
Methadone
Advantage of synthetic opioid?
Less dependence
(because opioid is addictive)
Methadone is also used to treat?
Heroin addiction
Substances that are synthesized in a laboratory, not from a biological source.
Synthetic opioids
Example of natural opioids?
Morphine
Codeine
Analgesic
Pain relief
Opioids are synthesized from?
opium poppy , (Papaver somniferum)
Opium poppy biological source
Papaver somniferum
Primarily for disinfecting and sterilization of surfaces and equipment; also used as a cold sterilant.
Glutaraldehyde
Cold sterilant targets.
Heat sensitive instruments
Used to preventing the painful and sometimes lethal vaso-occlusive crises associated with sickle cell disease.
Voxelotor
HBS meaning
sickle cell hemoglobin
What occurs when there are microcirculation obstructed by sickled RBCs causing ischemic injury to the organ causing pain?
lethal vaso-occlusive crises
sickled cell shape
crescent , meaning it is not flexible unlike normal RBCs.
ischemia meaning
lack of blood supply because blood flow is restricted so voxelotor prevents this phenomenon
Aldehydes and ketones are easily reduced to primary and secondary alcohols, respectively.
Aldehyde can be reduced into?
1° Alcohol, can be further oxidized into COOH.
Ketone can be reduced into?
2° Alcohol
Reduction of carbonyl compounds.
Aldehyde - 1° ROH
Ketone - 2° ROH
no reaction - 3° ROH
(opposite of oxidation reaction)
Most common metal hydrides used to reduce carbonyl compounds are?
lithium aluminum hydride (LiAlH₄)
sodium borohydride (NaBH4)
Oxidation of aldehydes gives a ___________ with the same number of carbon atoms.
carboxylic acid
Oxidizing agents used for the oxidation of carbonyl compounds.
Because the reaction occurs easily, many oxidizing agents, such as will work.
KMnO4 - Potassium permanganate
CrO3 - Chromium trioxide
Ag2O - Silver (1) Oxide
Peracids (aka peroxyacid)
Jones’ reagent oxidizes 2° ROH to?
Ketone
example:
2-propanol > Ketone
Nucleophiles can be negatively charged or neutral.
Examples of negatively charged nucleophiles.
Hydroxide
Hydride
Carbanion
Alkoxide
Cyanide
Examples of neutral nucleophiles.
Water
Alcohol
NH3 (Ammonia)
Amine
This attack the carbon atom of a carbon-oxygen double bond because that carbon has a partial positive charge.
Nucleophiles
The overall reaction involves addition of a nucleophile and a proton across the pi bond of the carbonyl group (when carried out in alcohol or water).
Nucleophilic Addition Reactions
Grignard Reagents
RMgX
R in RMgX can be?
Alkyl, allyl, vinyl & aryl
Mg in RMgX serves as?
Lewis acid of the reaction
X in RMgx stands for?
Halogen
Grignard reagents act as ____________ toward carbonyl compounds.
carbon nucleophiles
Main source of carbanion?
Grignards Reagent
Aldehydes gives 2° ROH except?
Formaldehyde (gives 1° ROH)
under Grignards Reagent
Addition of Hydrogen Cyanide (HCN) forms?
Cyanohydrins > RCH(OH)C≡N
He showed that cyanohydrin formation is said to be reversible and basecatalyzed.
Arthur Lapworth
Basecatalyzed means?
strong base is used instead of acid
Benzaldehyde cyanohydrin is also known as?
Mandelonitrile
Alcohols add to the C=O bond, the OR group becoming attached to the carbon and the proton becoming attached to the oxygen.
Formation of Hemiacetals and Acetals
Aldehydes and ketones react with alcohols to form, first, _______ and then, if excess alcohol is present, acetals.
hemiacetals
Acetals can be called _______, if derived from Ketone.
Ketals
Hemiacetals has _____ & ______ attached to the same carbon.
ether, alcohol
This have two ether functions at the same carbon atom.
Acetals
Organic compounds that have 2 hydroxyl groups on the same carbon atom.
Not stable, and will lose the H2O to reform the more stable carbonyl group.
Geminal Diols
Nitrogen nucleophile
Ammonia (NH3)
Substituted Ammonia (NH2-Y)
Used as an antipyretic before but it is found that it is toxic to blood cells, so it is now used to induce anemia to animal sudies.
Phenylhydrazine