Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 17.12, Problem 24P
Interpretation Introduction
Interpretation: The conversion of estrone to ethynylestradiol by the use of protecting group is to be stated.
Concept introduction:
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y-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since y-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. y-Butyrolactone shows an absorption in its IR spectrum at 1770 cm-1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of y-butyrolactone?
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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)CH3CH2CH2CO2H(l)+CH2CH3OH(l)⟶H+CH3CH2CH2CO2CH2CH3(l)+H2O(l)
A chemist ran the reaction and obtained 5.40 g of ethyl butyrate. What was the percent yield, The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.45g of butanoic acid and excess ethanol?
Chapter 17 Solutions
Organic Chemistry (6th Edition)
Ch. 17.1 - Prob. 1PCh. 17.2 - Which carbonyl groups in the anticancer drug taxol...Ch. 17.2 - Prob. 3PCh. 17.4 - Problem 20.4 What alcohol is formed when each...Ch. 17.4 - Problem 20.5 What aldehyde or ketone is needed to...Ch. 17.5 - Problem 20.8 Draw the products formed (including...Ch. 17.7 - Problem 20.10 Draw a stepwise mechanism for the...Ch. 17.7 - Prob. 10PCh. 17.7 - Problem 20.12 Draw the products formed from ...Ch. 17.7 - Prob. 12P
Ch. 17.7 - Prob. 13PCh. 17.8 - Prob. 14PCh. 17.8 - Problem-20.16 Review the oxidation reactions using...Ch. 17.9 - Problem-20.17 Write the step(s) needed to convert ...Ch. 17.9 - Prob. 18PCh. 17.10 - Problem 20.21 Draw the product of each reaction.
...Ch. 17.10 - Problem 20.22 Draw the products (including...Ch. 17.11 - Problem 20.23 What Grignard reagent and carbonyl...Ch. 17.11 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 17.11 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 17.12 - Prob. 24PCh. 17.13 - Problem 20.28 What ester and Grignard reagent are...Ch. 17.13 - Prob. 27PCh. 17.13 - Problem 20.30 What reagent is needed to convert ...Ch. 17.13 - Prob. 29PCh. 17.14 - What carboxylic acid formed from each alkyl halide...Ch. 17 - 20.37 Devise a synthesis of each alcohol from...Ch. 17 - 20.38 Draw the products formed when pentanal is...Ch. 17 - 20.39 Draw the product formed when is treated...Ch. 17 - The stereochemistry of the products of reduction...Ch. 17 - Prob. 40PCh. 17 - 20.42 Draw the products or each reduction...Ch. 17 - 20.44 Draw all stereoisomers formed in each...Ch. 17 - 20.54 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 57PCh. 17 - Prob. 58PCh. 17 - 20.57 What ester and Grignard reagent are needed...Ch. 17 - 20.58 What organolithium reagent and carbonyl...Ch. 17 - 20.59 What epoxide and organometallic reagent are...Ch. 17 - Prob. 62PCh. 17 - 20.69 An unknown compound A (molecular formula )...Ch. 17 - 20.70 Treatment of compound C (molecular formula )...
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