Fragrant Esters

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This lesson was written by 
Dr. Ryan White
Objectives 
Students will various types of esters by changing the identity of the “R” group on either side of the carboxyl group.
Procedure 

Chemistry                        Name ___________________________
Preparation of Fragrant Esters                Period ______            Score ____

Thought Question:  What determines the way something smells?

Introduction:  
Esters are a class of organic compounds that have characteristic sweet and fruity smells.  An ester contains a carboxyl group.  Today you will be making various types of esters by changing the identity of the “R” group on either side of the carboxyl group.

Pre-lab Questions:

  1. Draw the general structural formula for an ester:

Testable Question:  Will changing the shape (i.e. structural formula) of an ester change its fragrance?

Hypothesis:
_________________________________________________________________________________________________________________________________________________________________________________________________________

Materials:

  • 9 test tubes
  • Test tube clamp
  • Hot plate
  • 400 mL beaker
  • Methanol, ethanol and 1-pentanol
  • Acetic acid, salicylic acid and anthranilic acid

Procedure:

Follow these directions carefully!  Do not add more material than is listed.  

  • Make a 4 x 4 table in your lab notebook that takes up the entire page
  • Leave the top left box open name and draw the structural formulas for the alcohols we are using in this experiment in the remaining boxes in the top row
  • In the left hand column, draw the names and structures for the carboxylic acids we are using in this experiment (Leave the top right box open)
  • Number the boxes 1-9 and draw the appropriate structure and name…leave space to describe the smell.
  1. Label the test tubes with masking tape and number them 1 thru 9.
  2. Add 2 mL of alcohol to the appropriate test tubes.
  3. Add a spatula tip full of each acid to the appropriate test tubes.
  4. Carefully add 8 drops of sulfuric acid to each test tube.
  5. Warm the test tubes in a beaker of hot water (60 ºC) for 10 minutes.
  6. Cool the test tubes in an ice bath.
  7. Waft the aroma towards your nose with your hand, CAREFULLY!!!
  8. Record the results under Aroma.  Try to relate each odor to a familiar odor of a fruit, flower, or vegetable.

Post-lab questions:

  1. Was your hypothesis confirmed?  Why or why not?
  1. Why do you think the shape of a molecule affects its odor?  Discuss in 3-4 sentences.


TUBE         ALCOHOL               ACID          ESTER FRAGRANCE
----------------------------------------------------------------------
1           ethyl alcohol           acetic acid           fruity
2           methyl alcohol        salicylic acid       wintergreen
3           ethyl alcohol           benzoic acid        
4           n-amyl alcohol        salicylic acid       pineapple    (1-pentanol)
5           methyl alcohol        anthranilic acid   grape    (o-aminobenzoic acid)
6           n-amyl alcohol        acetic acid           banana    (1-pentanol)

Notes 
Sourced by sites.google.com/site/chemistryfortheworld Attribution-Noncommercial-Share Alike License.

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