CARBONYL AND AMINES Flashcards
(43 cards)
a carbon atom double-bonded to an oxygen atom
CARBONYL GROUP
- 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).
ALDEHYDE
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.
____________: 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.
- aromatic aldehydes
- benzaldehyde
- benzaldehyde
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
- Formalin
— 37% by mass or 40% by volume
FORMALDEHYDE
Naturally occurring
o ________ (vanilla flavoring)
o ________ (almond flavoring)
o ________ (cinnamon flavoring)
- Vanillin
- Benzaldehyde
- Cinnamaldehyde
- ___ & ___ 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
- C1 and C2; C3 through C11
- lower
- ______ 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
- Aldehydes and ketones; dipole–dipole attractions
- six; soluble
- soluble
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
- Cannirazo reaction
- Aldehydes; oxidation
- 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
- secondary alcohol
KETONES
Three ketones having additional common names
- acetone
- dimethyl ketone - acetophenone
- methyl phenyl ketone - benzophenone
- diphenyl ketone
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)
- Acetone
- miscible
- diabetes
- 2-heptanone
- Butanedione
- Carvone
CHEMICAL REACTION OF ALDEHYDES AND KETONES
- PREPARATION OF ALDEHYDES AND KETONES
- Oxidation
- Hemiacetal and acetal formation
- reduction
- Alcohol oxidation
OA
- air
- K2Cr2O7
- tollen’s solution
- benedict’s solution
OXIDATION
*Aldehyde —> carboxylic acid
*Ketone —> no reaction
- rx with one alcohol molecule produces a _________
- rx with 2 alcohol molecules produces an ________
- hemiacetal
- acetal
HEMIACETAL AND ACETAL FORMATION
*Aldehyde - hemiacetal - acetal
*Ketone - hemiacetal - acetal
- H2 gas is the reducing agent
- Ni, Pt, or Cu is the catalyst
REDUCTION
aldehyde - 1 alcohol
ketone - 2 alcohol
PREPARATION OF ALDEHYDES AND KETONES
- KMnO4 and K2Cr2O7 are common oxidizing agents
1* alcohol – aldehyde
2* alcohol – ketone
ALCOHOL OXIDATION
The simplest aromatic carboxylic acid – a benzene ring with a carboxyl group attachment – has the common name benzoic acid.
aromatic carboxylic acids
A carboxylic acid that contains one or more additional functional groups besides one or more carboxyl groups
Polyfunctional Carboxylic Acids
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)
- Acrylic acid
- Maleic acid
- Fumaric acid
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)
- glycolic acid
- lactic acid
- malic acid
- tartaric acid
- citric acid
- pyruvic acid
- 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.
- nine; sharp odor
- waxy solids; odorless
- Aromatic carboxylic acids and dicarboxylic acids
CARBOXYLIC ACID
negative ion produced when a carboxylic acid loses one or more acidic hydrogen atoms
carboxylate ions
- 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.
CARBOXYLATE ACID SALT
