3.3.5 Alcohols Flashcards

1
Q

How do you produce an alkene from an alcohol, what are the conditions?

A
  • via dehydration (eliminate water from alcohol)
  • require sulfuric acid or phosphoric acid catalyst

(e.g ethanol —> ethene + water)

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2
Q

How can alkenes be made from alcohols more sustainably?

A

By using alcohol that is made from fermentation of plants

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3
Q

What mechanism is undergone when you dehydrate alcohol? and what are the products

A

elimination mechanism
products : alkene , h2o, H+ (catalyst reformed)

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4
Q

Draw out the mechanism for the dehydration of ethanol

A
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5
Q

Why can dehydration of a non-primary alcohol lead to 2 different alkenes?

A

Cuz the double bond can be formed on either side of the carbon that the OH is attached to

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6
Q

What equipment + reagents is required for purifying the product of dehydrating alcohols and why

A

distillation- to separate the useful alkene from impurities (separates chemical by bpt)

separation funnel- despite distillation separating alkenes from impurities, further separation and purification may be needed (separates aqueous layers and organic layers)

drying agent- used to get rid of excess water that could remain

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7
Q

what are the steps to making cyclohexene

A

STEP 1 :
- DISTILLATION, add CONCENTRATED sulfuric or phosphoric acid and cyclohexanol into round bottomed flask. Add several anti-bumping granules to allow smooth boiling process (distributes heat evenly)

  • use heating mantle to warm reactants up to 83 degrees (bpt of cyclohexanol) (NO Bunsen burner AS ITS FLAMMABLE)
  • chemicals with bpt less than 83 degrees will evaporate, enter condenser and turn back into liquid
  • product collected in flask (cyclohexane) may have small impurities such as unreacted cyclohexanol and water

STEP 2 :
- SEPARATION, add products from step 1 into a SEPERATING FUNNEL . Add water to dissolve soluble impurities creating aqueous solution

  • after allowing the solution to settle, 2 LAYERS form (top layer = impure cyclohexene) (bottom layer = aqueous layer with water soluble impurities) Drain the aqueous layer off (ensure to remove stopper)

STEP 3:
- take the impure cyclohexene from step 2 and add to a round bottom flask

  • add ANHYDROUS CaCl2. this dehydrating agent will remove aqueous substances still remaining. (keep adding until no more clumps for (clumps due to cacl2 absorbing water))
  • INVERT flask and leave for 20-30mins
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8
Q

How are alcohols formed from Alkenes and what are the conditions

A

hydration of alkenes
requires steam and acid catalyst
300 degrees and pressure of 60atm

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9
Q

Why would fermentation be better than hydration to form an alcohol ?

A

Hydration uses an alkene formed from crude oil which is a non-renewable source (not sustainable)

Fermentation directly produces the alcohol from fermentation of glucose from plants.

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10
Q

What are 2 cons of fermentation?

A

Less yield of ethanol and slow process.
fractional distillation of ethanol at the end is also costly (still cheaper than other forms) and takes time

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11
Q

How does fermentation work?

A

it uses yeast in ANAEROBIC conditions (exothermic reaction) , the ethanol made then needs to undergo FRACTIONAL DISTILLATION to obtain pure ethanol

glucose –> ethanol + carbon dioxide

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12
Q

What are the conditions for fermentation and why?

A

temp at 30-40 degrees (yeast is an enzyme and this is the optimum temperature for the enzyme to work)

(at high temps the enzyme denatures and the reaction is too slow at lower temps)

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13
Q

Define biofuel

A
  • renewable energy source made from living materials
  • made from dead biological matter
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14
Q

Why are countries who plant lots of sugar cane bigger users of biofuels?

A

Sugar cane contains glucose which can be fermented by yeast to produce ethanol.
Bioethanol is added to petrol

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15
Q

What are 2 main advantages of biofuels

A
  1. they are renewable so they are more sustainable than crude oil
  2. they are carbon neutral (co2 released to make but co2 absorbed when growing sugar cane)
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16
Q

What are 2 main disadvantages of biofuels

A
  1. expensive to convert existing petrol engines to take fuels with higher conc of ethanol
  2. land used to grow sugar cane could have been used to grow food (food shortage)
17
Q

Why are biofuels almost carbon neutral not not completely?

A
  • during PHOTOSYNTHESIS, plants take in 6 mols of carbon dioxide 6CO2+6H2O→C6H12O6+6O2

-during FERMENTATION ethanol is made and 2 mols of carbon dioxide released
C6H12O6 (aq) 2C2H5OH(aq) + 2CO2

  • during combustion of ethanol 4 moles of carbon dioxide released
    2C2H5OH + 6 O2 → 4 CO2 + 6 H2O

6 mols co2 taken in and 6 mols co2 released BUT co2 is released when burning fossil fuels to transport biofuel cross-country, fossil fuels used to make fertiliser for crop and fuel used by machinery to harvest crop.

18
Q

What chemical is used to oxidise alcohols?

A

acidified potassium dichromate

19
Q

potassium dichromate being an oxidising agent gets reduced itself, hence what are the colour change it undergoes as it goes from Cr2o2 2- —> Cr3+?

A

orange to green

20
Q

What are primary and secondary and tertiary alcohols oxidised into

A

primary = aldehydes then carboxylic acid
secondary = ketone
tertiary = cant be oxidised

21
Q

What are primary and secondary and tertiary alcohols oxidised into

A

primary = aldehydes then carboxylic acid
secondary = ketone
tertiary = cant be oxidised

22
Q

What process is used to extract aldehyde when oxidising primary alcohol and why does this work

A

distillation
- we need to remove the aldehyde from the oxidising agent when it forms and distillation works as the aldehyde has a lower bpt than the alcohol

23
Q

How would you extract a carboxylic acid when oxidising a primary alcohol, why does this work

A

use reflux and excess acidified potassium dichromate
- reflux allows strong heating without losing volatile reactants and products as aldehydes that evaporate will condense and fall back into the flask

24
Q

How would you make ketone from oxidising a secondary alcohol

A

heat under reflux with acidified potassium dichromate

25
Q

Why will tollens and feelings solution produce a reaction with aldehydes but not ketones

A

because they are both oxidising agents and only aldehydes can further oxidise (to produce carboxylic acid) whereas ketones cannot further oxidise

26
Q

How is fehlings solution used to test between aldehydes and ketones

A

Fehlings solution is blue as it has Cu2+ ions

  • add it warm to the solution
    -if solution turns from blue to BRICK RED PRECIPITATE, aldehyde is present
  • if solution remains blue its a ketone
27
Q

How is tollens reagentused to test between aldehydes and ketones

A
  • add it warm to the solution
  • if solution forms a silver mirror, aldehyde is present (tollens has been reduced)
  • if solution remains unchanged then its a ketone