ALDEHYDES & KETONES Flashcards by Aliyah Dela Cruz

Aside from Aldehydes & Ketones, what are the other carbonyl containing compounds?

Carboxylic acid and its derivatives

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Have at least 1 hydrogen atom attached to the carbonyl carbon.

Aldehydes

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Have 2 carbon groups attached to the carbonyl carbon.

Ketones

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C=O is called

carbonyl carbon

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C=O with R group is called

Acyl group

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C=O with Hydrogen is called

Formyl group

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Aldehyde group is synonymous with?

Formyl group

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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

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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

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Bonded to a hydrogen (aldehyde) or another carbon (ketone).

Acyl group in Aldehydes & Ketones

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it CAN’T stabilize negative charge

Acyl group in Aldehydes & Ketones

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it CAN’T act as a leaving group in a nucleophilic substitution reaction

Acyl group in Aldehydes & Ketones

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Bonded to an atom (can be Oxygen, Halogen, Sulfur, Nitrogen).

Acyl group in Carboxylic Acid & Its Derivatives

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it CAN stabilize negative charge

Acyl group in Carboxylic Acid & Its Derivatives

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it CAN act as a leaving group in a nucleophilic substitution reaction

Acyl group in Carboxylic Acid & Its Derivatives

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Acyl group in carboxylic acid is bonded to an atom (can be ? ).

Oxygen, Halogen, Sulfur, Nitrogen

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In nomenclature, carbon 1 would be the carbon with?

Carbonyl carbon

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what suffix is added if the -CHO is attached to a cycloalkane

-carbaldehyde

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what suffic is added if the -CHO is attached to a benzene ring

-benzenecarbaldehyde

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Formaldehyde systematic name

Methanal

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Acetaldehyde systematic name

Ethanal

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Acrolein systematic name

Propenal

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Crotonaldehyde systematic name

2-Butenal

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Benzadehyde systematic name

Benzenecarbaldehyde

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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

ALDEHYDES & KETONES Flashcards

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