Acetate Synthesis Post Lab Questions:

 

The Cubs have been playing baseball in Chicago since 1870. During much of the time since then, they have played at Wrigley Field, which is the second-oldest ballpark in Major League Baseball (MLB) behind Boston's Fenway Park (1912). It was called Cubs Park from 1920 to 1926 before finally being renamed for the then Cubs team owner and chewing gum magnate William Wrigley Jr.

 

The 1906 Cubs won a record 116 of 154 games. They then won back to back World Series titles in 1907-08. They have not won a World Series since then, now over 100 years ago, and the Wrigley family believes that it is because people used to chew much more of their chewing gum in the early 1900s. In order to change the Cubs luck, they plan a nationwide marketing campaign to have everyone chew Wrigley's "Juicy Fruit" gum for next year's baseball season.

 

In order to produce the gum, the Wrigley company is soliciting a Request for Proposals (RFP) for the production of 10.0 metric tons of the Juicy Fruit flavoring.

 

They request a price estimate for this amount delivered to their Chicago factory in $/kg.

Dr. R.'s confidence in the knowledge, skill and ability that you have demonstrated in Chem 226 leads him to believe that you can compete for and win Wrigley's contract, perhaps earning a place in MLB history.

For the structure of the flavoring see:
http://chemconnections.org/organic/chem226/Labs/Smell/CC(=CCOC(=O)C)C.html
 
1) Draw a line structure for the ester.
2) Write a balanced equation using line stuctures for the reaction.
3) Provide a Table for the reactants, reagents, and products with IUPAC names, molecular formulas, molar masses and pertinent physical properties.
 
Estimate the cost to produce 10.0 metric tons of the acetate essence used for the Juicy Fruit flavoring, using the same reaction procedure that was employed for your experimental ester as a basis for the estimate. Chemical catalogues are available in the instrument room for you to base the raw material costs. Assume a 50% price discount for the large volumes of reagents that are to be purchased.

Questions:

a) How many kilograms of alcohol should theoretically be used? __________

b) How many kiloliters of glacial acetic acid should theoretically be used? __________

c) If the reaction is anticipated to produce a 90% yield, how many moles of the starting alcohol should be used to produce 10.0 metric tons of essence? _____________ How many kiloliters of glacial acetic acid ? _______________

d) What infrared peaks can be monitored to follow the reaction's progress?

For the disappearance of starting material ________ cm^-1

For the formation of product ________ cm^-1

The procedure that you based your estimate on was available the year that the Cubs last won a World Series. Organic synthesis has progressed dramatically during the past 100 years where environmental, energy and capital cost concerns have become very important in planning and process selection.

Consider the twelve guidelines below for "Green Chemistry", circle the items that could conceiveably be improved by using a different synthesis and write a sentence or two on how it might be accomplished.

Green Chemistry: Science and Politics of Change

Martyn Poliakoff, J. Michael Fitzpatrick, Trevor R. Farren, Paul T. Anastas
Science, Volume 297, Number 5582, Issue of 2 Aug 2002, pp. 807-810.
 
Green Chemistry Principles

1. It is better to prevent waste than to treat or clean up waste after it is formed.

2. Synthetic methods should be designed to maximize the incorporation of all materials used in the process into the final product.

3. Wherever practicable, synthetic methodologies should be designed to use and generate substances that possess little or no toxicity to human health and the environment.

4. Chemical products should be designed to preserve efficacy of function while reducing toxicity.

5. The use of auxiliary substances (e.g., solvents, separation agents, and so forth) should be made unnecessary wherever possible and innocuous when used.

6. Energy requirements should be recognized for their environmental and economic impacts and should be minimized. Synthetic methods should be conducted at ambient temperature and pressure.

7. A raw material or feedstock should be renewable rather than depleting wherever technically and economically practicable.

8. Unnecessary derivatization (blocking group, protection/deprotection, temporary modification of physical/chemical processes) should be avoided whenever possible.

9. Catalytic reagents (as selective as possible) are superior to stoichiometric reagents.

10. Chemical products should be designed so that at the end of their function they do not persist in the environment and break down into innocuous degradation products.

11. Analytical methodologies need to be developed further to allow for real-time in-process monitoring and control before the formation of hazardous substances.

12. Substances and the form of a substance used in a chemical process should be chosen so as to minimize the potential for chemical accidents, including releases, explosions, and fires.