ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 26, Problem 26.35P
Interpretation Introduction
Interpretation: A stepwise mechanism for the given reaction is to be drawn.
Concept introduction: The dihalocarbenes are synthesized by
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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). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.
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)
Given 8.50 g 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.
Lactones, cyclic esters such as compound A, are prepared byhalolactonization, an addition reaction to an alkene. For example,iodolactonization of B forms lactone C, a key intermediate in thesynthesis of prostaglandin PGF2α. Draw a stepwise mechanism for this addition reaction.
Chapter 26 Solutions
ORGANIC CHEMISTRY
Ch. 26 - Prob. 26.1PCh. 26 - Prob. 26.2PCh. 26 - Prob. 26.3PCh. 26 - Prob. 26.4PCh. 26 - Prob. 26.5PCh. 26 - Prob. 26.6PCh. 26 - Prob. 26.7PCh. 26 - Problem 26.8
What starting materials are needed to...Ch. 26 - Prob. 26.9PCh. 26 - Problem 26.10
What reagents are needed to convert...
Ch. 26 - Problem 26.11
What product is formed when each...Ch. 26 - Prob. 26.12PCh. 26 - Problem 26.13
Draw the products formed when each...Ch. 26 - Problem 26.14
What products are formed when ...Ch. 26 - Problem 26.15
Draw the product formed from...Ch. 26 -
What product is formed by ring-closing metathesis...Ch. 26 - Problem 26.17
What starting material is needed to...Ch. 26 - 26.18 In addition to organic halides, alkyl...Ch. 26 - 26.19 What product is formed by ring-closing...Ch. 26 - 26.20 Draw the products formed in each...Ch. 26 - What organic halide is needed to convert lithium...Ch. 26 - 26.22 How can you convert ethynylcyclohexane to...Ch. 26 - 26.23 What compound is needed to convert styrene...Ch. 26 - 26.24 What steps are needed to convert to octane...Ch. 26 - Prob. 26.25PCh. 26 - Prob. 26.26PCh. 26 - 26.27 Draw the products (including stereoisomers)...Ch. 26 - 26.28 Treatment of cyclohexene with and forms...Ch. 26 - Prob. 26.29PCh. 26 - 26.30 What starting material is needed to prepare...Ch. 26 - Prob. 26.31PCh. 26 - Prob. 26.32PCh. 26 - When certain cycloalkenes are used in metathesis...Ch. 26 - 26.34 Draw the products formed in each reaction.
...Ch. 26 - Prob. 26.35PCh. 26 - Draw a stepwise mechanism for the following...Ch. 26 - Sulfur ylides, like the phosphorus ylides of...Ch. 26 - Although diazomethane is often not a useful...Ch. 26 - Prob. 26.39PCh. 26 - Prob. 26.40PCh. 26 - Prob. 26.41PCh. 26 - Prob. 26.42PCh. 26 - 26.43 Devise a synthesis of each compound using a...Ch. 26 - 26.44 Devise a synthesis of each compound from...Ch. 26 - 26.45 Devise a synthesis of each compound from...Ch. 26 - 26.46 Devise a synthesis of each substituted...Ch. 26 - Biaryls, compounds containing two aromatic rings...Ch. 26 - Prob. 26.48PCh. 26 - 26.49 Draw the product formed from the...Ch. 26 - Prob. 26.50PCh. 26 - 26.51 Devise a synthesis of each of the following...Ch. 26 - Prob. 26.52PCh. 26 - 26.53 The following conversion, carried out in the...Ch. 26 - Prob. 26.54PCh. 26 - 26.55 Dimethyl cyclopropanes can be prepared by...Ch. 26 - Prob. 26.56P
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- a) b) d) 4. Draw the correct structure of the alcohol starting material that would give the following oxidized products: H A ora forarrow_forwardName the structure. Heating compound A in the presence of H2SO4 results in which product?arrow_forwardwith one stage (single reaction), butane can be prepared from: a) butanol-1 b) butanoic acid c) buten-1 d) butanol-2arrow_forward
- Ethers (general formula R—O—R)have many important uses. Until recently,methyl tert-butyl ether (MTBE, right)was used as an octane booster and fueladditive for gasoline. It increases the oxy-gen content of the fuel, which reducesCO emissions. MTBE is synthesized bythe catalyzed reaction of 2-methylpropene with methanol.(a) Write a balanced equation for the synthesis of MTBE. (Hint:Alcohols add to alkenes similarly to the way water does.)(b) If the government required that auto fuel mixtures contain2.7% oxygen by mass to reduce CO emissions, how many gramsof MTBE would have to be added to each 100. g of gasoline?(c) How many liters of MTBE would be in each liter of fuel mix-ture? (The density of both gasoline and MTBE is 0.740 g/mL.)(d) How many liters of air (21% O₂ by volume) are needed at24C and 1.00 atm to fully combust 1.00 L of MTBE?arrow_forwardSynthesize each compound from benzonitrile (C6H5CN) as the only organic starting material; that is, every carbon in the product must originate in benzonitrile.arrow_forwardEthyl 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?arrow_forward
- 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…arrow_forwardEthyl 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…arrow_forwardThe reaction of p-cresol with CH2=O resembles the reaction of phenol (PhOH) with CH2=O, except that the resulting polymer is thermoplastic but not thermosetting. Draw the structure of the polymer formed, and explain why the properties of these two polymers are so different.arrow_forward
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