Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 22, Problem 2LGP

Shikimic acid is a key biosynthetic intermediate in plants and microorganisms. In nature, shikimic acid is converted to chorismate, which is then converted to prephenate, ultimately leading to aromatic amino acids and other essential plant and microbial metabolites (see the Chapter 21 Learning Group problem). In the course of research on biosynthetic pathways involving shikimic acid, H. Floss (University of Washington) required shikimic acid labeled with 13 C to trace the destiny of the labeled carbon atoms in later biochemical transformations. To synthesize the labeled shikimic acid, Floss adapted a synthesis of optically active shikimic acid from D-mannose reported earlier by G. W. J. Fleet (Oxford University). This synthesis is a prime example of how natural sugars can be excellent chiral starting materials for the chemical synthesis of optically active target molecules. It is also an excellent example of classic reactions in carbohydrate chemistry. The Fleet–Floss synthesis of D - ( ) - [ 1 , 7 - 13 C ] -shikimic acid (1) from D-mannose is shown in Scheme 1.

(a) Comment on the several transformations that occur between d-mannose and 2. What new functional groups are formed?

(b) What is accomplished in the steps from 2 to 3, 3 to 4, and 4 to 5?

(c) Deduce the structure of compound 9 (a reagent used to convert 5 to 6), knowing that it was a carbanion that displaced the trifluoromethanesulfonate (triflate) group of 5. Note that it was compound 9 that brought with it the required 13 C atoms for the final product.

Chapter 22, Problem 2LGP, Shikimic acid is a key biosynthetic intermediate in plants and microorganisms. In nature, shikimic

SCHEME 1 The synthesis of D - ( ) - [ 1 , 7 - 13 C ] -shikimic acid (1) by H. G. Floss, based on the route of Fleet et al. Conditions:

(a) acetone, HA;

(b) BnCl, NaH;

(c) HCl, aq. MeOH;

(d) N a l O 4 ;

(e) N a B H 4 ;

(f) ( C F 3 S O 2 ) 2 O , pyridine;

(g) 9, NaH;

(h) H C O O N H 4 + P d / C ;

(i) NaH;

(j) 60% aq. C F 3 C O O H .

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Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple.  Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Part A Given 7.30 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures.   Part B A chemist ran the reaction and obtained 5.95 gg  of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures.   Part C The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 7.30 gg of…
Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple.  Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Given 8.45 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures.   A chemist ran the reaction and obtained 5.50 gg  of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures.   The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 8.45 gg of butanoic acid and excess…
Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) a) Given 7.70 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100% yield? b) A chemist ran the reaction and obtained 5.25 g of ethyl butyrate. What was the percent yield? c) The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.70 g of butanoic acid and excess ethanol?
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