organic chemisrty Flashcards
halogenalkane –> nitrile
reagent: KCN
Conditions: ethanol and heat under reflux
Type: nucleophilic substitution
halogenalkane –> amine
reagent: conc NH3
conditons: ammonia, heat in a sealed tube
type: nucleophilic substitution
nitrile –> carboxylic acid
Reagent: dilute HCl
Conditions: heat under reflux
Type: hydrolysis
primary alcohol –> carboxylic acid
conditions: reflux and heat
reagents: primary alcohol and acidified potassium dichromate
at the end distill off the carboxylic acid
type; oxidation
observation: orange –> green
ester –> carboxylic acid + water
Reagents: dilute acid catalyst
conditions: heat under reflux (and distill off the carboxylic acid)
type: hydrolysis
acyl chloride –> carboxylic acid + HCl
Reagents: water
type: hydrolysis
observations: toxic misty fumes
Conditions: room temp still a violent reaction
amides –> carboxylic acid + ammonium salt
reagents: (water +) dilute HCl
type: acidic hydrolysis
amides –> carboxylate salt + ammonia
reagents: dilute NaOH
type: alkaline hydrolysis
observations: distinctive ammonia smell. Turns red litmus blue
carboxylic acid + phosphorous pentachloride –> acyl chloride + phosphorous trichloride oxide + Hydrogen chloride gas
Reagents: PCl5 (s)
products: phosphorous trichloride oxide - colourless liquid
Observations: HCl (g) misty fumes
test: turns blue litmus –> red
glass rod dipped in conc NH3 –> WHITE SMOKE
Carboxylic acid + base –> salt +water
CH3COOH + NaOH –> CH3COONa + H2O
carboxylic acid + carbonate –> carbon dioxide + water + salt
2CH3COOH + CaCO3 –> Ca(CH3COO)2 + H2O + CO2
FIZZING - CO2
Carboxylic acid + alcohol –> ester + water
Reagents: alcohol, strong catalyst e.g. conc H2SO4
conc H2SO4 is a dehydrating agent it removes H2O therefore shifting position of eq to the RHS therefore yield of ester increases
Conditions: reflux
Carboxylic acid + lithium tetrahydridoaluminate (III) –> alchol + water
reagents: LiAlH4
Conditions: Dry ether
acyl chloride + alcohols –> Ester + HCl (g)
Type: addition-elimination
Condition: reflux in dry anhydrous conditions
Acyl chloride + conc Ammonia –> primary amide + HCl
Conditions: low temperature + excess conc ammonia
type: addition - elimination
Acyl chloride +amine –> N-substituted amide + HCl
Conditions - anhydrous
Observations: misty fumes
hydrolysis of esters using an acid cataylst
Reversible reaction
conditions: reflux - dilute H+ catalyst
Hydrolysis of esters using a basic catalyst -
more efficient - not reversible because the carboxylate salt and alcohol do not react with each other
liberate acid by adding a strong acid salt
Why do acyl chlorides react with alcohols faster than carboxylic acids do?
- C-Cl bond is weaker than C=O bond
2. C delta positive in carbonyl is more delta positive therefore more attractive to nucleophiles