ORGANIC CHEMISTRY SOLUTIONS MANUAL
5th Edition
ISBN: 9781260367546
Author: SMITH
Publisher: MCG CUSTOM
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Textbook Question
Chapter 10, Problem 10.63P
Bromoetherification, the addition of the elements of
constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether
antibiotic monensin (Problem 21.37). Draw a stepwise mechanism for the following intramolecular
bromoetherification reaction.
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Bromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings
containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 21.36).
Draw a stepwise mechanism for the following intramolecular bromoetherification reaction.
Br
Br2
+
HBr
Bromoetherication, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 21.37). Draw a stepwise mechanism for the following intramolecular bromoetherication reaction.
Draw a stepwise mechanism for the formation of A from an alcohol and acid chloride. A was converted in one step to blattellaquinone, the sex pheromone of the female German cockroach Blattella germanica.
Chapter 10 Solutions
ORGANIC CHEMISTRY SOLUTIONS MANUAL
Ch. 10 - Prob. 10.1PCh. 10 - Problem 10.2 How many degrees of unsaturation are...Ch. 10 -
Problem 10.3 How many degrees of unsaturation...Ch. 10 - Give the IUPAC name for each alkene. abcdeCh. 10 - Give the IUPAC name for each polyfunctional...Ch. 10 - Problem 10.6 Label each C-C double bond as E or Z....Ch. 10 - Prob. 10.7PCh. 10 - Prob. 10.8PCh. 10 - Prob. 10.9PCh. 10 - Problem 10.10 Rank the following isomers in order...
Ch. 10 - Linolenic acidTable 10.2 and stearidonic acid are...Ch. 10 - Prob. 10.12PCh. 10 - Problem 10.13 What product is formed when each...Ch. 10 - Prob. 10.14PCh. 10 - Problem 10.15 Draw the products formed when each...Ch. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Addition of HBr to which of the following alkenes...Ch. 10 - Problem 10.19 Draw the products, including...Ch. 10 - Prob. 10.20PCh. 10 - Problem 10.21 What two alkenes give rise to each...Ch. 10 - Prob. 10.22PCh. 10 - Problem 10.23 Draw the products of each reaction,...Ch. 10 - Problem 10.24 Draw all stereoisomers formed in...Ch. 10 - Prob. 10.25PCh. 10 - Problem 10.26 What alkylborane is formed from...Ch. 10 - Draw the products formed when each alkene is...Ch. 10 - What alkene can be used to prepare each alcohol as...Ch. 10 - Prob. 10.29PCh. 10 - Draw the products of each reaction using the two...Ch. 10 - Problem 10.31 Devise a synthesis of each compound...Ch. 10 - Give the IUPAC name for each compound. a.b.Ch. 10 - a Label the carbon-carbon double bond in A as E or...Ch. 10 - Prob. 10.34PCh. 10 - 10.35 Calculate the number of degrees of...Ch. 10 - Prob. 10.36PCh. 10 - Label the alkene in each drug as E or Z....Ch. 10 - Give the IUPAC name for each compound. a. c. e. b....Ch. 10 - Prob. 10.39PCh. 10 - 10.40 (a) Draw all possible stereoisomers of, and...Ch. 10 - Prob. 10.41PCh. 10 - 10.42 Now that you have learned how to name...Ch. 10 - Prob. 10.43PCh. 10 - Prob. 10.44PCh. 10 - Prob. 10.45PCh. 10 - Draw the products formed when (CH3)2C=CH2 is...Ch. 10 - What alkene can be used to prepare each alkyl...Ch. 10 - Prob. 10.48PCh. 10 - Draw the constitutional isomer formed in each...Ch. 10 - Prob. 10.50PCh. 10 - Draw all stereoisomers formed in each reaction. a....Ch. 10 - Draw the products of each reaction, including...Ch. 10 - Prob. 10.53PCh. 10 - Prob. 10.54PCh. 10 - Prob. 10.55PCh. 10 - 10.56 Draw a stepwise mechanism for the following...Ch. 10 - Prob. 10.57PCh. 10 - Draw a stepwise mechanism for the conversion of...Ch. 10 - Draw a stepwise mechanism that shows how all three...Ch. 10 - Less stable alkenes can be isomerized to more...Ch. 10 - Prob. 10.61PCh. 10 - Prob. 10.62PCh. 10 - Bromoetherification, the addition of the elements...Ch. 10 - Devise a synthesis of each product from the given...Ch. 10 - 10.65 Draw a synthesis of each compound from...Ch. 10 - 10.66 Explain why A is a stable compound but B is...Ch. 10 - Prob. 10.67PCh. 10 - Prob. 10.68PCh. 10 - 10.69 Lactones, cyclic esters such as compound A,...Ch. 10 - 10.70 Draw a stepwise mechanism for the following...Ch. 10 - 10.71 Like other electrophiles, carbocations add...Ch. 10 - 10.72 Draw a stepwise mechanism for the...
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- Draw a stepwise mechanism for the formation of A from an alcohol and acid chloride. A was converted in one step to blattellaquinone, the sex pheromone of the female German cockroach, Blattella germanica.arrow_forwardOne step in the synthesis of the antihistamine fexofenadine (Section 23.5) involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.arrow_forwardAziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiflu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y.arrow_forward
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