Topic 10: Reactions of Alkanes, alkenes, alcohols
but-2-ene + hydrogen→ (with heat and Ni catalyst)
--> butane (a hydrogenation addition rxn)
butene + water --> (with H2SO4 catalyst)
--> butanol
Butene + water (steam) → (with concentrated H2SO4 as a catalyst)
--> butanol (addition reaction)
propane + chlorine (with UV light) -->
--> chloropropane + HCl (a substitution rxn)
cyclohexene + hydrogen gas → (with heat and Ni catalyst)
--> cyclohexane (addition)
ethene + water --> (with sulfuric acid catalyst)
--> ethanol
ethanoic acid (heated with LiAlH4 in dry ether)-->
--> ethanol (a reduction rxn)
bromoethane + NaOH →
--> ethanol + sodium bromide (Sn2 substitution)
Oxidation of Methanol with acidified dichromate -->
--> forms methanal (kept via reflux)---> then forms methanoic acid
ethene + hydrogen iodide -->
--> iodoethane (addition)
benzene + nitronium (NO2+) -->
--> nitrobenzene
Oxidation of 2-methylpropan-2-ol with acidified dichromate -->
--> no reaction (it's a tertiary alcohol)
ethene + ethene →
--> polyethene
oxidation of Propan-2-ol with acidified dichromate -->
--> propanone
propanol + butanoic acid --> (with concentrated H2SO4 as a catalyst)
--> propyl butanoate (condensation rxn)
propan-2-one (heated with aqueous NaBH4)-->
-> propan-2-ol (a reduction rxn)
propanoic acid (heated with LiAlH4 in dry ether)-->
-> propanol (a reduction rxn)
propane + chlorine → (with UV)
1-chloropropane (or 2-chloropropane) + HCl (free radical substitution)
Primary alcohol oxidising agent
Acidified Dichromate
Primary alcohols oxidised to
Aldehyde then carboxylic acid
Method used to obtain aldehyde from Primary alcohol
Distill off aldehyde upon production
Method used to obtain carboxylic acid from Primary alcohol
Heat under reflux
butan-2-one (heated with aqueous NaBH4)-->
--> 2-butanol (a reduction rxn)
2-fluoropropane + sodium hydroxide →
--> 2-propanol + sodium fluoride (either Sn1 or Sn2 substitution)
ethene + chlorine -->
--> 1,2 dichloroethene
Secondary alcohols oxidised to
Ketones
Esterification
The reaction of an alcohol with a carboxylic acid to produce an ester and water.
The condition needed for chlorine and ethane to react together to form chloroethane.
UV light
chiral
a carbon joined to four different atoms or groups.
homolytic fission
a covalent bond breaks and the shared electron pair splits evenly producing 2 free radicals
racemic mixture
a mixture of two enantiomers in equal amounts and is optically inactive.
a test which will distinguish between alkanes and alkenes
add bromine water
polarimeter
an instrument for measuring the ability of a compound to rotate the plane of polarized light
bromine goes colorless when added to this type of organic molecule
any alkene
This kind of solvent is best for an Sn2 reaction
aprotic solvents because they do not form hydrogen bonds and will easily dissolve the K+1 or Na+1 rather than the OH-1 electrophile
The products that form when propane, C3H8, undergoes incomplete combustion in a limited amount of air.
carbon monoxide, water
examples of nucleophiles
chloride ion, hydroxide, ammonia, water
Diastereomers
configurational isomers that are are not mirror images of each other.
enantiomers
configurational isomers that are mirror images of each other.
why alkenes are reactive
electron dense area in the pi bond attracts electrophiles, pi bond is relatively weak
examples of electrophiles
hydrogen ion, NO2+ , H3O+
a free radical species
it is uncharged, formed from homolytic fission, has an unpaired electron
ultimate product of the reduction of nitrobenzene
phenylamine
examples of aprotic solvents (they do not form hydrogen bonds)
propanone, ethanenitrile (CH3CN)
This kind of solvent is best for an Sn1 reaction
protic solvents because they can form hydrogen bonds to stabilize the positively charged carbocation intermediate
why alkanes are relatively unreactive
strong, nonpolar bonds do not attract other species
Esterification catalyst
sulfuric acid
optical activity
the rotation of plane-polarized light by a chiral molecule
propene + chlorine →
→ 1, 2 dichloropropane
ethane + bromine → (with UV)
→ bromoethane + HBr
Ethanol + methanoic acid → (with concentrated H2SO4 as a catalyst)
→ ethyl methanoate + water
methanol + propanoic acid → (with concentrated H2SO4 as a catalyst)
→ methyl propanoate + water (an esterification rxn)
