Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 13, Problem 43P
a. What five-carbon alkene forms the same product whether it reacts with HBr in the presence of a peroxide or with HBr in the absence of a peroxide?
b. Draw the structures of four six-carbon
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2. The following carbocation is generated as an intermediate in the addition of H-Br to an alkene.
Draw the structure of all possible alkenes that could have formed this intermediate.
10. Draw an energy diagram for the addition of HBr to 1-pentene. Let one curve on your diagram show the
formation of 1-bromopentane product and another curve on the same diagram show the formation of 2-
bromopentane product. Draw and label the positions for all reactants, intermediates, and products.
Which curve has the higher-energy carbocation intermediate? Which curve has the higher-energy first
transition state?
4. What is the major organic product obtained from the following reaction?
1. NaNH,
2. CH₂CH₂Br
+
0
5. What is the major organic product obtained from the following reaction?
1. BH3
2. H₂O₂, NaOH
Chapter 13 Solutions
Organic Chemistry
Ch. 13.2 - Prob. 1PCh. 13.2 - Write the steps for formation of...Ch. 13.3 - Prob. 3PCh. 13.4 - Prob. 4PCh. 13.5 - Prob. 7PCh. 13.5 - a. Would chlorination or bromination produce a...Ch. 13.5 - Prob. 10PCh. 13.6 - Prob. 11PCh. 13.7 - Prob. 12PCh. 13.7 - Prob. 13P
Ch. 13.8 - Prob. 14PCh. 13.8 - Draw the stereoisomers of the major...Ch. 13.9 - a. How many stereoisomers are formed from the...Ch. 13.9 - Prob. 17PCh. 13.9 - Prob. 19PCh. 13.9 - Prob. 20PCh. 13.9 - Prob. 21PCh. 13.10 - Prob. 22PCh. 13.11 - How many atoms share the unpaired electrons in...Ch. 13.11 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - Prob. 26PCh. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - Prob. 31PCh. 13 - Prob. 32PCh. 13 - Prob. 33PCh. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Starting with cyclohexane, how could the following...Ch. 13 - a. Propose a mechanism for the following reaction:...Ch. 13 - What stereoisomers are obtained from the following...Ch. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Draw the products of the following reactions,...Ch. 13 - a. What five-carbon alkene forms the same product...Ch. 13 - Prob. 44PCh. 13 - Prob. 45PCh. 13 - Prob. 46PCh. 13 - Explain why the rate of bromination of methane...Ch. 13 - Prob. 48P
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- What about the second step in the electrophilic addition of HCl to an alkene-the reaction of chloride ion with the carbocation intermediate? Is this step exergonic or endergonic? Does the transition state for this second step resemble the reactant (carbocation) or the product (alkyl chloride)? Make a rough diagram of what the transition state may look like?arrow_forward4. A CHEM 245 student wants to synthesize some ethylene glycol to use as antifreeze in his radiator this winter. He proposes the following reaction to his instructor, who quickly explains that this reaction won't work as proposed due to the student's choice of reagent. 1) NaH 2) H20 OH Но a) Why can't sodium hydride (NaH) be used as the nucleophile in the reaction above? b) Propose an alternate reagent that COULD be used with the ethylene oxide to successfully give the desired ethylene glycol product.arrow_forwardA. REACTIONS OF ALKENES- provide the product(s) or reagents that are needed to accomplish the following transformations CH3 1. BH 3, THF 2. H₂O₂, NaOH, H₂Oarrow_forward
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