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)