Tag Archives: esters

Chapter 10: Organic reactions: pathways to new products

10.1 Reactions of Alkanes

Alkanes contain strong carbon-carbon single bonds and strong carbon-hydrogen bonds. There are no partial charges on alkane molecules that might initiate reactions. The effect is that alkanes only undergo very few reactions.

(1) Combustion of alkanes

Alkanes can undergo combustion, producing CO2(g) and H2O(g)

When asked to create a combustion equation for a particular fuel, do the following steps:

  1. Write the fuel’s molecular formula
  2. Add excess O2(g)
  3. Produce CO2(g) and H2O(g)
  4. Balance C, H and O in that order.
  5. REMEMBER TO INCLUDE ALL THE STATES!

General formula: alkane + O2(g) → CO2(g) + H2O(g)

Example: C6H14(l) + O2(g) → 6CO2(g) + 7H2O(g) (halves are okay!)

(2) Substitution of alkanes

Alkanes can also undergo substitution, in which one of the hydrogen atoms is replaced with a halogen (e.g. F, Cl, Br, or I).

General formula: alkane + X2 → chloroalkane

Example: CH3CH3(g) + Cl2(g) + UV light → CH3CH2Cl(g) + HCl(g) (note that HCl is a gas!)

10.2 Reactions of alkenes

(1) Addition of alkenes

Alkenes can under addition reactions with halogens, hydrogen gas or water.

addition reactions of alkenes
Source: VCEasy.org

The first reaction happens at room temperature. If you have a gaseous alkene like ethene, you can bubble it through either pure liquid bromine or a solution of bromine in an organic solvent like tetrachloromethane. The reddish-brown bromine is decolourised as it reacts with the alkene.

(2) Addition polymerisation of alkenes
Source: Chemhume.co.uk

Chemguide links

Chemguide is an excellent revision resource that goes a little further than VCE. Read the relevant Chemguide pages below.

http://www.chemguide.co.uk/organicprops/alkanemenu.html
http://www.chemguide.co.uk/organicprops/alkenemenu.html
http://www.chemguide.co.uk/organicprops/estermenu.html

10.3 Oxidising ethanol to ethanoic acid

You will need to memorise the following ways to oxidise an alkanol into a carboxylic acid.

3 ways to oxidise alcohols
Source: VCEasy.org

For more information, visit this Chemguide page.

10.4: Making Esters

Table of Esters and their Smells
Click to enlarge

10.5: Organic Reaction Pathways

making esters from alkenes
Source: VCEasy.org

10.6: Fractional distillation

Fractional distillation can be used to separate compounds with different boiling points. It is commonly used in the separation of the compounds contained within crude oil.

More information about fractional distillation can be found here.

When hydrochloric acid is added to propene, two products can be produced: 1-chloropropane and 2-chloropropaneOnly the 1-chloropropane can be made into a carboxylic acid. We must therefore separate the 1-chloropropane from the 2-chloropropane by fractional distillation.

When reacting alkenes with 3 or more carbons (such as propene) with hydrochloric acid, we must write “HCl and fractional distillation” on the arrow.

For example:

propane fractional distillation
Source: Heinemann Chemistry 2

Click here for a 4-minute explanatory video about fractional distillation (beyond the VCE Chemistry course).

Read: Heinemann Chemistry 2 Chapter 10

Infographic: Table of Esters and Their Smells v2 (200+ smells!)

Table of Esters and Their Smells v2
Click to download the high-res PDF version (1.8Mb)

This updated version of my Table of Esters and Their Smells contains 200+ smells from nearly as many esters.

Best of all are the phenylacetates that I’ve added, which smell like honey, chocolate and jasmine. I’ve also freshened up the fonts and added text labels where they were necessary. Take a look! 🙂

If you have any questions about this chart, just drop me an email or join the Reddit discussion here.

Feel free to use it as you wish. 😉

Infographic: Table of Esters and their Smells

Table of Esters and Their Smells

Click to download (1.1Mb JPEG)

I love esters. This infographic is totally self-explanatory to any chemist. (Or email me if you have any questions.) Enjoy! 😉

  • Esters are made by reacting alcohols and carboxylic acids together in a condensation reaction.
  • Different combinations of alcohols and carboxylic acids give rise to different esters, and each ester has a unique aroma.
  • These esters are found naturally in fruits and vegetables and are also used in perfumes.
  • You can now look up an ester in the table above and find its aroma by referring to the picture.
  • Ambiguous or “mixed” smells are indicated by the presence of multiple images in each box.
  • Benzyl salicylate is amazing: some people can perceive it while others can’t. However, people who can’t perceive benzyl salicylate can tell that it alters the overall aroma of perfume to which it’s been added! Magic!
  • You can make any of these relatively safely in the kitchen or at school.
  • All of these esters are edible in minuscule (microgram) amounts and are found naturally in all fruits, vegetables, herbs and spices.
  • That said, though,
      never eat anything you make in the lab!