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(SLU) PHARMA 113: Chem Lec > CARBONYL AND AMINES > Flashcards

CARBONYL AND AMINES Flashcards

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1
Q

a carbon atom double-bonded to an oxygen atom

A

CARBONYL GROUP

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2
Q
  • One of the two additional bonds that the carbonyl carbon atoms forms must be to a hydrogen atom and the other may be to a hydrogen atom, an alkyl or cycloalkyl group, or an aromatic ring system.
  • The C in the notation RCHO is the carbonyl carbon atom. It is bonded to the R group (single bond), the H atom (single bond), and the O atom (double bond).
A

ALDEHYDE

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3
Q

Cyclic aldehydes are NOT possible.

For an aldehyde carbonyl carbon atom to be part of a ring system, it
would have to form two bonds to ring atoms, which would give it five bonds.

A
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4
Q

____________: compounds in which an aldehyde group is attached
to a benzene ring - are named as derivatives of _________, the parent compound

  • The last of these compounds is named as a __________ rather than as a phenol because the aldehyde group has priority over the hydroxyl group.
A
  • aromatic aldehydes
  • benzaldehyde
  • benzaldehyde
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5
Q

o Simplest aldehyde

o Oxidized from methanol

o Irritating gas

o _________
- Aqueous solution w answer
- ____ by mass or ____ by volume
- Uses: biological specimen preservative, embalming fluid

A
  • Formalin
    — 37% by mass or 40% by volume

FORMALDEHYDE

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6
Q

Naturally occurring

o ________ (vanilla flavoring)
o ________ (almond flavoring)
o ________ (cinnamon flavoring)

A
  • Vanillin
  • Benzaldehyde
  • Cinnamaldehyde
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7
Q
  • ___ & ___ aldehydes are gases at room temperature, ___ through ____ straight-chain saturated aldehydes are liquid, and the higher aldehydes are solids.
  • The presence of alkyl groups tends to ______ both boiling points and melting points, as does the presence of unsaturation in the carbon chain.
  • Lower-molecular-mass ketones are colorless liquids at room temperature
A
  • C1 and C2; C3 through C11
  • lower
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8
Q
  • ______ and ______ have higher boiling points than alkanes because of ____________ between molecules.
  • Aldehydes and ketones having fewer than ___ carbon atoms are ________ in both organic solvents and water.
  • When six or more carbon atoms are present, such compounds are _______ in organic solvents but not in water
A
  • Aldehydes and ketones; dipole–dipole attractions
  • six; soluble
  • soluble
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9
Q

Reactions of Aldehyde and Ketones

  • Undergone _________
  • ________ are oxidized to carboxylic acids and reduced to primary alcohol while ketones are resistant to _______
  • Some carbohydrates could also have aldehydes on their structure
A
  • Cannirazo reaction
  • Aldehydes; oxidation
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10
Q
  • Both of the additional bonds of the carbonyl carbon atom must be to another carbon atom that is part of an alkyl, cycloalkyl, or aromatic groups
  • Product of oxidation of __________
  • Non-termna functional group
  • General condensed formula is RCOR
  • Unlike aldehydes, ketones can form cyclic structures
A
  • secondary alcohol

KETONES

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11
Q

Three ketones having additional common names

A
  1. acetone
    - dimethyl ketone
  2. acetophenone
    - methyl phenyl ketone
  3. benzophenone
    - diphenyl ketone
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12
Q

o ________, a colorless, volatile liquid with a pleasant, mildly “sweet” odor, is the ketone used in largest volume in industry

o An excellent solvent because it is ______ with both water and nonpolar solvent.

o It is a major component of some nail-polish removers.

o The presence of this in urine is a sign of _______

NATURALLY OCCURING
o ________ (clove flavoring – from eugenol, used as a toothache drop)
o ________ (butter flavoring)
o ________ (spearmint flavoring – flavorant, perfumery)

A
  • Acetone
  • miscible
  • diabetes
  • 2-heptanone
  • Butanedione
  • Carvone
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13
Q

CHEMICAL REACTION OF ALDEHYDES AND KETONES

  • PREPARATION OF ALDEHYDES AND KETONES
A
  1. Oxidation
  2. Hemiacetal and acetal formation
  3. reduction
  • Alcohol oxidation
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14
Q

OA
- air
- K2Cr2O7
- tollen’s solution
- benedict’s solution

A

OXIDATION

*Aldehyde —> carboxylic acid
*Ketone —> no reaction

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15
Q
  • rx with one alcohol molecule produces a _________
  • rx with 2 alcohol molecules produces an ________
A
  • hemiacetal
  • acetal

HEMIACETAL AND ACETAL FORMATION

*Aldehyde - hemiacetal - acetal
*Ketone - hemiacetal - acetal

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16
Q
  • H2 gas is the reducing agent
  • Ni, Pt, or Cu is the catalyst
A

REDUCTION

aldehyde - 1 alcohol
ketone - 2 alcohol

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17
Q

PREPARATION OF ALDEHYDES AND KETONES

  • KMnO4 and K2Cr2O7 are common oxidizing agents
A

1* alcohol – aldehyde
2* alcohol – ketone

ALCOHOL OXIDATION

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18
Q

The simplest aromatic carboxylic acid – a benzene ring with a carboxyl group attachment – has the common name benzoic acid.

A

aromatic carboxylic acids

19
Q

A carboxylic acid that contains one or more additional functional groups besides one or more carboxyl groups

A

Polyfunctional Carboxylic Acids

20
Q

UNSATURATED ACIDS

  • _________: paints, starting material for polymers
  • _________: ionization forms salt found in antihistamine medication
  • _________: metabolic acid (intermediate compounds in the metabolic reactions that
    occur in the human body)
A
  • Acrylic acid
  • Maleic acid
  • Fumaric acid
21
Q

HYDROXY ACIDS

  • _________: sugar cane and sugar beets
  • _________: souring of milk, sauerkraut, and dill pickles
  • _________: apple (fruit of trees of the genus Malus)
  • _________: grapes
  • _________: citrous fruits
  • _________: second metabolic acid (simplest keto acid)
A
  • glycolic acid
  • lactic acid
  • malic acid
  • tartaric acid
  • citric acid
  • pyruvic acid
22
Q
  • Most polar organic compound
  • Very high BP and MP – due to the hydroxyl group
  • Unsubstituted saturated monocarboxylic acids containing up to ___ carbon atoms are liquids that have strong, sharp odors.
  • Acids with 10 or more carbon atoms in an unbranched chain are ________ that are odorless (because of low volatility).
  • _____________, as well as ____________, are also odorless solids.
A
  • nine; sharp odor
  • waxy solids; odorless
  • Aromatic carboxylic acids and dicarboxylic acids

CARBOXYLIC ACID

23
Q

negative ion produced when a carboxylic acid loses one or more acidic hydrogen atoms

A

carboxylate ions

24
Q
  • Ionic compound in which the negative ion is a carboxylate ion
  • Carboxylate salts do NOT directly kill microorganisms present in food.
  • Rather, they prevent further growth and proliferation of these organisms by increasing the pH of the foods.
A

CARBOXYLATE ACID SALT

25
Q

o ___________ – mold and yeasts growth in beverages, jams and jellies (solid preparations, tablets, capsules)

o ___________ – inhibit mold and yeast in dairy products, dried fruits, sauerkraut, and some meat and fish (semi-solid, suspensions)

o ___________ – baked products, cheese, spreads

A
  • Benzoic salts of sodium and potassium
  • sorbates
  • calcium and sodium propionates
26
Q

A carboxylic acid derivative in which the -OH portion of the carboxyl group has been replaced with an -OR group.

A

ESTERS

27
Q

Condensation reaction of a carboxylic acid with an alcohol (or phenol) to produce an ester and
water. A strong acid catalyst (generally sulfuric acid) is needed.

A

esterification

28
Q
  • closed-ring structured ether
  • indicated using a Greek letter
  • _________: five membered ring
  • _________: six-membered lactone ring system
A
  • y-lactone
  • s-lactone

LACTONE

29
Q

Flavor/Fragrance Agents

o _______: pleasant odor of newly mown hay

o _______: taste and odor of ripe peaches

A
  • coumarin
  • 4-decanolide
30
Q

Pheromones

o ________ – alarm pheromone for the honey bee

o ________ – sexual attractant for canine species

o ________ (catnip plant) – attractant for cats of all types

A
  • Isoamyl acetate
  • Methyl p-hydroxybenzoate
  • Nepetalactone
31
Q

Medications

o ________– local anesthetic

o ________ (analgesic and wintergreen (counterirritant) - esters of salicylic acid

o ________– large-ring lactone, antimicrobial

A
  • Benzocaine
  • Aspirin
  • Erythromycin
32
Q

an ester reacts with water, producing the carboxylic acid an alcohol from which the ester was formed

A

ESTER HYDROLYSIS

33
Q

hydrolysis of an organic compound, under basic conditions, in which a carboxylic acid salt is one of the products

A

ESTER SAPONIFICATION

34
Q

different from the other compounds in that the element nitrogen, in addition to carbon,
hydrogen, and oxygen, is present

A

AMIDES

35
Q

an organic derivative of ammonia (NH3) in which one or more alkyl, cycloalkyl, or aryl groups are attached to the nitrogen atom

A

amine

36
Q

Functional group present in a primary amine, the -NH2 group, is called an __________

Secondary and tertiary amines possess __________

A
  • amino group
  • substituted amino groups
37
Q

A benzene ring bearing an amino group is called ________

A

aniline

38
Q

The methylamines (mono-, di-, and tri-) and ethylamine are ______ at room temperature and have ammonia-like odors.

Most other amines are liquids, and many have odors resembling that of raw fish

A few amines, particularly _______, have strong, disagreeable odors.
o The foul odor arising from dead fish and decaying flesh is due to amines released by the bacterial
decomposition of protein.

o “odoriferous” compounds are the diamines _________ and _________

A
  • gases
  • diamines
  • putrescine and cadaverine
39
Q
  • The _______ amines are irritating to the skin, eyes, and mucous membranes and are toxic by ingestion.
  • _________ amines are generally toxic: readily absorbed through the skin and affect both the blood and the nervous system.
A
  • simpler
  • Aromatic
40
Q

an ionic compound in which the positive ion is a mono-, di-, or trisubstituted ammonium ion (RNH3, R2NH2, or R3NH) and the negative ion comes from an acid

Preparation: evaporating the water from the acidic solutions

A

amine salts

41
Q

NEUROTRANSMITTERS

o ___________
- found in the brain
- deficiency causes Parkinson’s disease
- drug ______, pass through the BBB giving relief from Parkinson’s disease

o ___________
- treat life-threatening low blood pressure that occurs when a person goes into septic shock

o ___________
- involved in sleep, sensory perception, and the regulation of body temperature

A
  • Dopamine ; L-dopa
  • Norepinephrine
  • Serotonin
42
Q

CNS STIMULANTS

o ___________
- Immediate treatment for anaphylactic shock resulting from a severe allergic reaction to a bee sting, a drug, or even peanuts.

o ___________
- increases alertness, concentration, and overall cognitive performance while decreasing fatigue

o ___________
- treatment of ADHD

A
  • Epinephrine
  • Amphetamine
  • Methamphetamine
43
Q

2 decongestants

A
  • pseudoephedrine
  • phenylephrine

(SLU) PHARMA 113: Chem Lec (17 decks)

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