SAS 6-10 (physical, chemical properties & reactions)

SAS6

PHENOLS: physical properties

low melting solids

Oily liquids

Colorless solids w/ medicinal odor

SLIGHTLY: soluble in H2O

CANNOT BE DEHYDRATED; NOT REACT TO OXIDIZING AGENTS

CAN BE OXIDIZED: stronger oxidizing agents

ACIDITY is imporant: it is a WEAK ACID

ALCOHOLS & PHENOLS: Flammable

USES OF PHENOLS: antiseptics, antioxidant food additives, flavoring agents or antibacterials

ACID IONIZATION OF PHENOL: negative ion produced from ionization(phenoxide ion)

PHENOL +H2O-> PHENOXIDE ION +H3O+

BASIC IONIZATION: (Sodium phenoxide) produe when phenol react w/ NAOH

PHENOL +NAOH(aq)-> SODIUM PHENOXIDE

PHENOL DERIVATIVES: o-Phenylphenol & 2-benzyl-4chlorophenol present in LYSOL

SAS 7

PHYSICAL PROPERTIES: ETHERS

Boiling point is similar to alkanes

More soluble in water than alkanes of similar molecular mass (ether form hydrogen bonds w/ water)

WATER SOLUBILITY: similar to alcohols

CHEMICAL PROPERTIES:

FLAMMABLE

Diethyl ether: boiling point @ 35 degreescelsius yet if above room temp: FLASH FIRE HAZARD

REACT SLOWLY W/ OXYGEN from the air to form: unstable hydroperoxides & peroxides

PHYSICAL PROPERTIES OF THIOLS:

Lower Boiling points than alcohols

Strong disagreable odor

FAMILIAR ODOR: Natural Gas -> (results from ADDITION OF LOW CONCENTRATION OF METHANETHIOL TO GAS)

easily oxidized BUT yield diff. products than alcohol analogs

FORMS DISULFIDE

SAS 8

PHYSICAL & CHEMICAL PROPERTIES OF ALDEHYDES & KETONES:

(aldehydes)

C1 & C2 are gases @ room temp

C3-C11 straight chain saturated aldehydes are liquids

HIGHER are solids

LOW MOLECULAR MASS: pungent, penetrating, unpleasant odors

HIGH MOLECULAR MASS (Above C8); more fragrant like benzaldehyde derivatives

(KETONES)

Low molecular mass: colorless liquids @ room temp

Odor: pleasant

generally used: perfumes & air fresheners

(BOTH)

Presence of alkyl groups & unsaturation in the carbon chain: ; LOWER boiling & melting point

BOILING POINTS ARE INTERMIDIATE: between alcohols & alkanes of similar molecules

HIGHER BP: than alkanes since dipole-dipole attractions between molecules

LOWER BP: than alcohols since NO HYDROGEN BONDINGS occurs on alcohols

BP of similar molecular mass:

ALCOHOLS > carbonyl compounds > alkanes

BOTH OXIDATION: OA-> KMnO4 & K2Cr2O7

Primary alc-> aldehydes-> COOH

Secondary alc-> KETONES

TERTIARY-> no reaction

BOTH REDUCTION: RA/Catalyst-> Ni, Pt, Cu

Aldehydes-> Primary alc

Ketones-> secondary alcohols

TOLLENS TEST or Silver Mirror Test: solutions contains AgNO3+NH4 in H2O

-> w/n added to aldehyde the Ag+ ion (OA) reduced to Silver Metal w/c DEPOSITS the inside and

FORMS-> Silver Mirror (+ presence of aldehyde)

BENEDICTS TEST: Cu2+ ion is REDUCED to Cu+

PRECEPITATES solution as Cu2O -> brick red color

SOLUTION: DISSOLVING copper sulphate, sodium citrate & sodium carbonate in H2O

SAS 9

CARBOXYLIC ACID: Physical Properties

Polar: carbonyl & hydroxyl are polar

VERY HIGH MELTING POINT & BOILING POINT

Unsubstituted saturated monocarboxylic acids CONTAINS-> UP TO C9 are LIQUIDS, Sharp, Strong ODORS

unbranched chain ACIDS UP TO C10-> WAXY SOLIDS, odorless (due to volatility)

AROMATIC COOH like dicarboxylic acid-> ODORLESS SOLIDS

PREPARATION: OA-> CrO3/K2Cr2O7

Primary alc-> aldehydes-> COOH

Aromatic acids-> can be prepared by OXIDIZING a alkyl group on a benzene derivative

ESTERS: Physical Properties

MOLECULES CANT FORM HYDROGEN BONDS: DO NOT EXHIBIT HYDROGEN BONDED TO OXYGEN

BP-> lower than alcohols & COOH of comparable molecular mass

SOLUBILITY: rapidly Decreases w/ increasing carbon chain length (REACHED-> C3 - C5 in the chain)

LOW & HIGH MOLECULAR MASS-> colorless liquids

USES: flavor & fragrance of fruits & flowers (caused mixture of ester:natural flavor/odor)

SYNTHETIC PRODUCTION on the basis of flavoring agents on esters-> ice cream, gelatins, soft drinks....

REACTION OF ESTERS: involves (ESTER HYDROLYSIS/ SAPONIFICATION)

-> BREAKING the carbon-oxygen single bond (C-O) holding the ALCOHOL part & Acid part

ESTER HYDROLYSIS: react w/ H2O-> COOH & alcohol (requires catalyst/enzyme-> a STRONG ACID)

ESTER SAPONIFICATION: UNDER BASIC CONDITIONS NAOH/KOH-> alcohol+ COOH SALT

SAS 10

AMINES: physical properties

-> foul odor arising from DEAD FISH is due to amines RELEASED by the Bacterial decomposition of protein

-> BP; LOWER than alcohols

-> fewer C6 are INFINITELY soluble in H2O

ODORIFEROUS COMPOUNDS-> Diamines putrescine & Cadaverine

Methylamines & ethylamines: gases at room temp & ammonia odor

AMINES like diamines-> liquids that are resembling of raw fish odor w/ are strong, disagreable odor

SIMPLER AMINES-> irrirating to SKIN & MUCOUS MEMBRANE; TOXIC by Ingestion

AROMATIC AMINES-> TOXIC

BASICITY: like ammonia are WEAK BASE -> accepting proton H+ from H2O -> Ammonia Ion (NH4+) & Hydroxide Ion (OH+)

EXAMPLE: methylamine+ H2O-> Methylammonium ion +Hydroxide Ion

RESULT of amine w/ H2O-> basic soln containing substituted NH4+ & OH+

Reaction of ACID w/ Base -> SALT

Amines/ Aromatic amines +ACID-> AMINE SALT

PROTONATION (treated w/ acid)-> amine gains hydrogen -> amine salt

DEPROTONATION (treated w/ base)-> amine salt loses hydrogen-> amine

Amine (protonation) amine salt

Amine salt (deprotonation) amine

ALKYLATION presence of BASE:

AMMONIA + alkyl halide -> PRIMARY amine (reaction of ethyl bromide REMOVED from the REACTION MIXTURE; N atom of amine REACT to alkyl halide -> secondary & tertiary

PRIMARY amine + alkyl halide -> SECONDARY amine

SECONDARY amine + alkyl halide -> TERTIARY amine

TERTIARY amine + alkyl halide -> QUATERNARY AMMONIUM SALT (NEEDS A STRONG BASE(NAOH) TO PRODUCE)

AMIDES: physical properties

-> DO NOT EXHIBIT Basic Properties in solutions

->Methanamide & N,N-dimethyl derivatives (SIMPLEST; primary, secondary, tertiary amides); are LIQUDS

-> UNBRANCHED Primary Amides (except methanamides)-> SOLIDS

-> MELTING POINT; HIGHER than COOH

PREPARATION:

-> LESS REACTIVE than COOH

-> SYNTHESIZED from; Acid chloride, acid anhydride, ester, COOH.

REACTION-> elevated at 100 degress celsius +dehydrating agent is present

NH3 + COOH -> primary amide

Primary amide +COOH -> Secondary amide

Secondary amide +COOH -> Tertiary amide

IF NO AMIDE FORMATION:

ACID + PRIMARY AMINE (25degrees)-> COOH SALT/ION

AMIDIFICATION REACTION/ CONDENSATION REACTION: OH group is LOST from COOH & H atom is LOST from ammonia/amine & H2O formed

COOH +AMINE/AMMONIA -> AMIDE

AMIDE HYDROLYSIS: bond between carbonyl (c=o) & Nitrogen is BROKEN -> Free Acid +Free Amine (CATALYST: acids, base or enzymes)

ACID/BASIC HYDROLYSIS

;Acid Conditions convert amine -> amine salt

;Basic Conditions convert COOH -> COOH salt (called; amide saponification)