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Esters. Kaitlyn Picavet, Natalie Williamson, Sidney Wittman, Vivian Ly. General Structure. O R – C – O – R’ T he general formula of an ester is written as RCOOR’ Where RCO = carboxylic acid And where OR’= alcohol . ||.

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esters

Esters

Kaitlyn Picavet, Natalie Williamson, Sidney Wittman, Vivian Ly

general structure
General Structure

O

R – C – O – R’

  • The general formula of an ester is written as RCOOR’

Where RCO = carboxylic acid

And where OR’= alcohol

||

nomenclature
Nomenclature
  • Esters are made up of 2 alkyl groups and 2 oxygen atoms.
  • The alkyl groups and oxygen come from the carboxylic acid and alcohol used in esterification (the formation of esters).

Ethanol + Butanoic Acid  Ethyl Butanoate + Water

Alcohol Carboxylic Acid Ester

the name follows the pattern yl oate
The name follows the pattern ____yl____oate
  • The first blank comes from the alcohol-drop the -anol-add -ylie) ethanol would be ethyl.
  • The second blank comes from the carboxylic acid-drop the -oic-add -oateie) butanoic acid would become butanoate
  • (drawings on white board)
drawing rules
Drawing Rules
  • Drawing esters combines drawing Alcohols and drawing Carboxylic Acids.
  • The alkyl with the –oate is double bonded to an oxygen atom. The alkyl with the –yl has an oxygen atom incorporated in it.

O

O

OH

+

+

OH

H-OH

O

Butanoic Acid

Ethanol

Ethyl Butanoate

physical and chemical properties
Physical and Chemical Properties
  • Low polarity
  • Not as polar as alcohols
  • Dipole-Dipole, London dispersion
  • In Hydrogen bond, esters can only act as Hydrogen acceptors, not donors
  • Unsaturated fats/oils always have at least one C=C double bond
slide7

Similar boiling points to ketones and Aldehydes

  • As chain length increases, solubility in water decreases
  • Solid form: Fat
  • Liquid form: Oil
  • Fats have a higher boiling point
slide8
Uses
  • Esters are known for the odours of fruits, flowers, cosmetics and perfumes.
  • Esters are also used in fats and oils.
  • Synthetic esters are added as flavourings to processed foods.
  • They are good compounds for polar organic compounds like; printing ink and cement.
examples
Examples
  • Apple- methyl butanoate

CH3CH2CH2COOCH3

  • Banana- 3-methylbutyl ethanoate

CH3

|

CH3COOCH2CH2CHCH3

  • Cherry- ethyl benzoate

C6H5COOC2H5

  • Pineapple- ethyl butanoate

CH3CH2CH2COOCH2CH3

  • Rum- ethyl methanoate

CH3CH22CH2CH2CH2CH2COOCH2CH3

reactions esterification
Reactions: Esterification
  • Neutralization/condensation reaction

carboxylic acid + alcohol ----------> ester + water

O

|| – OH + R–OH--------> RC–O–R + HOH

RC

heat

catalyst

organic base

O

organic salt

||

heat

catalyst

reactions hydrolysis
Reactions: Hydrolysis
  • Ester treated with acid or base: reversal of esterification occurs (split into acid & alcohol)
  • Products:sodium salt of acid + alcohol

RC–O–R + NaOH- ------> RC–O- + Na+ + R–OH

O

||

O

||

ester

base

acid

alcohol

reactions saponification
Reactions: Saponification
  • Fats and oils are esters of long-chain acids:
  • When heated with a strong base, saponification occurs & produces soap.
references
References

AUS-e-TUTE. (n.d.) Chemistry Tutorial: Esters and Esterification. Retrieved from the Web 29/09/11. http://www.ausetute.com.au/esters.html

Clark, J. (2004). Introducing Esters. Retrieved from the Web 22/09/11. http://www.chemguide.co.uk/organicprops/esters/background.html

Kimble, M.G. (2008). Esterification Reactions. Retrieved from the Web 29/09/11. http://www.ipfw.edu/chem/112/kimble/5-Synthesis%20of%20Esters.pdf

Snelling, C.R. (2002). Synthesis of an Ester: Fischer Esterification. Retrieved from the Web 29/09/11. http://www2.volstate.edu/msd/CHE/242/Labs/Ester.htm

van Kessel, H., Jenkins, F., Davies, L., Plumb, D., Di Giuseppe, M., Lantz, O., & Tompkins, D. (2003). Nelson Chemistry 12. Toronto: Nelson Thomson Canada Limited.