EX 8: ALCOHOLS Flashcards
organic compounds composed of an aliphatic carbon atom with a HYDROXYL (-OH) functional group
ALCOHOL
functional group of all alcohols
HYDROXYL GROUP
general formula for alcohols
ROH
- very COMMON and may exist FREELY in nature
- exhibit some unique set of physicochemical properties mainly due to the presence of the hydroxyl functional group
- some of the properties of alcohols depend on the LENGTH of the alkyl chain attached to the hydroxyl group
ALCOHOLS
active component of alcoholic beverages
ETHANOL (ethyl alcohol)
general formula for primary (1°) alcohol
RCH2OH
general formula for secondary (2°) alcohol
R2CHOH
general formula for tertiary (3°) alcohol
R3COH
C with the –OH group attached to ONE other carbon atom
primary (1°) alcohol
C with the –OH group attached to TWO other carbon atoms
secondary (2°) alcohol
C with the –OH group attached to THREE other carbon atoms
tertiary (3°) alcohol
PRIMARY ALCOHOL oxidation process
alcohol —> aldehyde —> carboxylic acid
SECONDARY ALCOHOL oxidation process
alcohol —> ketone
enzyme that inactivate the substance
ALCOHOL DEHYDROGENASE
- antabuse
- used by people with chronic alchoholism
DISULFIRAM
Boiling point of ALCOHOL
HIGHER than hcs
the solubility of alcohols is governed by its ability to perform ___________ with polar solvents
INTERMOLECULAR H-BONDING
usually formed in between the OH group of alcohol and water
H-BONDS
the LONGER the alkyl chain is, the _____ the alcohol becomes soluble with water
LESSER
the ______ the alkyl chain is, the LESSER the alcohol
becomes soluble with water
LONGER
the longer the alkyl chain is, the lesser the alcohol becomes _________ with water
SOLUBLE
alcohols are acidic in nature e because of their ability to react with _____
ACTIVE METALS
what forms when alcohols react with active metals
ALKOXIDE
alcohol acidity is due to the ______
POLARITY OF THE HYDROXYL BOND
what happens to the acidity of alcohol when an ELECTRON DONATING group is attached to the hydroxyl group as the electron density increases on the oxygen atom
ACIDITY DECREASES
primary alcohols are ______ acidic than secondary and tertiary alcohols
MORE ACIDIC
alcohols exhibit a range of spontaneous chemical reactions due to the _____ of C-O and O-H bonds
CLEAVAGE
used to distinguish PRIMARY and SECONDARY alcohols from tertiary alcohols
JONES TEST (CHROMIC ACID TEST)
also known as CHROMIC ACID TEST
JONES TEST
JONES TEST is named after
EWART JONES
Jones reagent
CrO3 (chromium oxide) in H2SO4
POSITIVE RESULT in JONES TEST
BLUE-GREEN SOLN
JONES TEST:
1° alcohols and aldehydes are oxidized to _________
CARBOXYLIC ACID
JONES TEST:
2° alcohols are oxidized to
KETONES
JONES TEST:
the ___________ (Cr6+) is REDUCED to a BLUE-GREEN TRIVALENT chromium (Cr3+) species, which often precipitates in acetone
ORANGE HEXAVALENT
JONES TEST:
the orange hexavalent chromium (Cr6+) is reduced to a ___________ chromium (Cr3+) species, which often precipitates in acetone
BLUE-GREEN TRIVALENT
JONES TEST:
the orange hexavalent chromium (Cr6+) is reduced to a blue-green trivalent chromium (Cr3+) species, which often precipitates in _____
ACETONE
used as PRESERVATIVES in VACCINES but NOT used in NEONATES because it can cause GASPING SYNDROME
benzyl alcohol
used to distinguish TERTIARY and SECONDARY alcohols from primary alcohols
LUCAS TEST
Lucas reagent
ZnCl2 in concentrated HCl
Lucas test is named after
HOWARD LUCAS
POSITIVE RESULT in LUCAS TEST
turbid solution/formation of two layers
LUCAS TEST:
SN1 mechanism to produce ____________________ which appears as white precipitate or cloudiness of the solution; benzyl, allylic and propargylic alcohols often give immediate results like tertiary alcohols
INSOLUBLE ALKYL CHLORIDE
LUCAS TEST:
SN1 mechanism to produce insoluble alkyl chloride which appears as ________________ of the solution; benzyl, allylic and propargylic alcohols often give immediate results like tertiary alcohols
WHITE PPT OR CLOUDINESS
LUCAS TEST:
SN1 mechanism to produce insoluble alkyl chloride which appears as white precipitate or cloudiness of the solution; benzyl, allylic and propargylic alcohols often give _________________ like tertiary alcohols
IMMEDIATE RESULTS
used to demonstrate REACTIVITY OF ALCOHOLS WITH CARBOXYLIC ACID when heated with acid catalyst
ESTERIFICATION
POSITIVE RESULT in ESTERIFICATION:
methanol w/ salicylic acid
MINTY ODOR (methyl salicylate)
POSITIVE RESULT in ESTERIFICATION:
esters
FRUITY-LIKE ODOR
principle of esterification
reaction is both SLOW & REVERSIBLE
demonstrate OXIDATION OF ALCOHOLS through partial oxidation and dehydrogenation using hot catalyst (heated copper)
TEST FOR METHANOL
TEST FOR METHANOL: POSITIVE RESULT
RED-VIOLET RING; DARK RED PPT
TEST FOR METHANOL method was introduced by
ROBERT MULLIKEN
TEST FOR METHANOL:
methanol is oxidized to _______ (formaldehyde) using heated copper as catalyst; to detect if methanol was oxidized, resorcinol is added to the solution and a concentrated sulfuric acid) is added dropwise to induce color change, precipitates and layer formation
METHANAL
TEST FOR METHANOL:
methanol is oxidized to methanal (formaldehyde) using ___________ as catalyst; to detect if methanol was oxidized, resorcinol is added to the solution and a concentrated sulfuric acid) is added dropwise to induce color change, precipitates and layer formation
HEATED COPPER
TEST FOR METHANOL:
methanol is oxidized to methanal (formaldehyde) using heated copper as catalyst; to detect if methanol was oxidized, ___________ is added to the solution and a concentrated sulfuric acid) is added dropwise to induce color change, precipitates and layer formation
RESORCINOL
TEST FOR METHANOL:
methanol is oxidized to methanal (formaldehyde) using heated copper as catalyst; to detect if methanol was oxidized, resorcinol is added to the solution and a concentrated sulfuric acid) is added ______ to induce color change, precipitates and layer formation
DROPWISE
used to identify METHYL KETONES or secondary alcohols adjacent to a methyl group
IODOFORM TEST
Wagner’s reagent (WIKI)
IODINE IN POTASSIUM IODIDE
IODOFORM TEST:
used to decolorize the solution
NaOH (sodium hydroxide)
IODOFORM TEST:
POSITIVE RESULT
turbid yellow solution/canary yellow precipitate
IODOFORM TEST:
I2 in KI in NaOH reacts only for compounds with the structure RCH(OH)CH3 or RC=OCH3 to form _______ (canary yellow precipitate); does not work for all alcohols or ketones and does not work also for water-insoluble compounds
IODOFORM
does not work for all alcohols or ketones and does not work also for water-insoluble compounds
IODOFORM TEST
used to detect the presence of GLYCEROL
ACROLEIN TEST
- a POLYHYDROXY ALCOHOL (TRIOL) obtained as a by-product from the manufacture of SOAP used as a MOISTURIZING AGENT in cosmetic formulations
- component of fats
GLYCEROL
ACROLEIN TEST:
POSITIVE RESULT
PUNGENT ACRID ODOR
ACROLEIN TEST:
when heated with ______________, glycerol is dehydrated to form propenal (acrolein)
POTASSIUM BISULFATE (KHSO4)
ACROLEIN TEST:
when heated with potassium bisulfate (KHSO4), __________ is dehydrated to form propenal (acrolein)
GLYCEROL
ACROLEIN TEST:
when heated with potassium bisulfate (KHSO4), glycerol is ________ to form propenal (acrolein)
DEHYDRATED
ACROLEIN TEST:
when heated with potassium bisulfate (KHSO4), glycerol is dehydrated to form ________ (acrolein)
PROPENAL