Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 11, Problem 11.68P
Explain why an optically active solution of
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When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone, why
Explain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.
When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone.
Why doesn’t the cis isomer yield the oxide?
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Draw structures for the three alkynes having...Ch. 11 - Prob. 11.2PCh. 11 - Give the IUPAC name for each compound.Ch. 11 - Give the structures corresponding to each of the...Ch. 11 - Prob. 11.5PCh. 11 - Prob. 11.6PCh. 11 - Which bases can deprotonate acetylene? The pKa...Ch. 11 - Draw the organic products formed when each alkyne...Ch. 11 - Prob. 11.9PCh. 11 - Problem 11.9 Draw the products formed when is...
Ch. 11 - Explain the following result. Although alkenes...Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.13PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.15PCh. 11 - Prob. 11.16PCh. 11 - Prob. 11.17PCh. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.19PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.21PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.23PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.25PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - Prob. 11.27PCh. 11 - Give the IUPAC name for each alkyne.Ch. 11 - Prob. 11.29PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.31PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.33PCh. 11 - Prob. 11.34PCh. 11 - Prob. 11.35PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - Draw the products formed when 3-hexyne is treated...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - What alkynes give each of the following ketones as...Ch. 11 - Prob. 11.41PCh. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - Prob. 11.43PCh. 11 - Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.45PCh. 11 - Prob. 11.46PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.52PCh. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - Prob. 11.55PCh. 11 - Synthesize each compound from acetylene. You may...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.61PCh. 11 - Prob. 11.62PCh. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.65PCh. 11 - Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.67PCh. 11 - 11.65 Explain why an optically active solution of ...
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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?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) 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_forward
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