Alcohol production Flashcards
Wha
What will we produce if we react Z-pent-2-ene with water?
pentan-2-ol or pentan-3-ol
These are examples of
addition reactions bcs we are adding a molecule (water) can also be called hydration reaction
& when a molecule loses water it’s a dehydration reaction
How do industries carry out hydration reaction?
- they add the alkene in its gas phase into the reactor
- they add water in the form of steam (g)
- add an acid catalyst (H+) to start the reaction
What can sulfuric acid act as?
electrophile
What happens if we react propene with water using sulfuric acid as our catalyst knowing that sulfuric acid acts as an electrophile?
carbon carbon bond breaks and a carbon hydrogen bond forms
causing H-O to break
making the electron pair go to Oxygen making it a long pair
Between these 2 molecules (propen-2-ene and propen-1-ene) what molecule would likely form
First molecule (propen-2-ene) as secondary carbocations are more stable than primary carbocations meaning the secondary carbocation would form majority of the time
Knowing that secondary is more stable, what would happen next in the mechanism?
because we are also reacting water
a water bond would form between the carbocation like this
arrow telling us C—O bond forms
What happens next after water bonds with the molecule of propene
The Lone pair attracts one of the H+ ions and forms a bond breaking the H—O bond
The complete mechanism memorise
from propene to propan-2-ol
- catalyst H forms a bond with the double bond of carbon forming a carbocation
- carbocation forms a bond with water
- lone pair of catalyst forms a bond of one Hydrogen and that hydrogen breaks the bond with oxygen
Because sulfuric acid is a reagent at the beginning of the reaction and a product at the end, its acting as a
catalyst
because H2SO4 (sulfuric acid) is acting as an electrophile, this is an example
of electrophilic addition reaction
mechanism of all reactions using sulfuric acid
How do we simplify this to make it easier rather than writing whole sulfuric acid out?
H+
What’s the most appropriate mechanism for this reaction?
As the acid wasn’t specified this is the correct answer
What’s wrong with this mechanism?
1) arrow is the other way around
2) Oxygen is missing a lone pair
3) Oxygen is missing a + bcs it has 3 bonds
What’s the equation for this reaction
CH2=CHCH2CH2CH3+H2O <=> CH3CH(OH)CH2CH2CH3
What’s the equation for the hydration of butene?
C4H8 + H2O <=> C4H9OH
What do we do when writing equations for ethene, propene and ethanol?
we just write their molecular formula as they don’t have position isomer
What’s the equation for the hydration of propene to propan-1-ol
C3H6 + H2O <=> CH3CH2CH2OH
Industries use a degree of 300 celsius which is a compromised temperature why is that so?
this reaction is exothermic as stated (-45 kJmol)
so if we lower the temperature the equilibrium position will shift to the right
and increase the yield of ethanol
However low temperatures also decrease the rate of reaction so industries use 300 as a compromise between yield and rate