Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 10, Problem 10.17P
Interpretation Introduction
Interpretation: The reaction of
Concept introduction: The reaction of hydrogen halide with
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When 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.
When 1-chlorocyclohexene reacts with HBr, the major product is 1-bromo- 1-chlorocyclohexane. Propose a mechanism for this reaction, and explain why your proposed intermediate is more stable than the other possible intermediate.
When 1-cyclohexylethanol is treated with concentrated aqueous HBr, the major product is 1-bromo-1-ethylcyclohexane. How would you convert 1-cyclohexylethanol to (1-bromoethyl) cyclohexane in good yield?
Chapter 10 Solutions
Organic Chemistry
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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- Describe the stereochemistry of the bromohydrin formed in each reaction (each reaction is stereospecific). (a) cis-3-Hexene + Br2/H2O (b) trans-3-Hexene + Br2/H2Oarrow_forwardPropose a mechanism for the reaction of(a) 1-methylcyclohexanol with HBr to form 1-bromo-1-methylcyclohexane.(b) 2-cyclohexylethanol with HBr to form 1-bromo-2-cyclohexylethane.arrow_forward2- Mention the product of a nucleophilic substitution reaction of (S)-2-bromohexane with acetate ion, CH3CO2- Assume that inversion of configuration occurs, and show the chemistry of both the reactant and product. 3- Draw the mechanism of the SN2 Reaction. Show the correct directions of the arrows, and all reagents. 4- Draw the mechanism of the SN1 Reaction. Show the correct directions of the arrows, and all reagents. 5- Draw the mechanism of the E2 Reaction with an Alkyl Halide. Show the correct directions of the arrows, and all reagents. 6- Draw the mechanism of the E1 Reaction with an Alkyl Halide. Show the correct directions of the arrows, and all reagents. 7- Mention the product formed in an SN2 reaction between 1-bromobutane and NaI. 8- Rank the following compounds in order of their expected reactivity toward SN2 reaction: CH3Br, CH3OTos, (CH3)2CHCl. 9- Explain Grignard Reagents in details with one example. 10- Mention how a halogen substituent can be replaced by a deuterium atom…arrow_forward
- Reaction of hbr with 2-methylpropene yields 2 bromo 2 methylpropane. What is the structure of the carbocation formed during the reaction? Show the mechanism of reaction.arrow_forwardDraw the major product(s) of the reaction of 1-methylcyclohexene with the following reagents, disregarding stereoisomers: 1. NBS/∆/peroxide 2 . Br2/CH2Cl2 3. HBr 4. HBr/peroxideb. For each reaction, show which stereoisomers are obtained.arrow_forwardReaction of HBr with 2-methylpropene yields 2-bromo-2-methylpropane. What is the structure of the carbocation formed during the reaction? Show the mechanism of the reaction.arrow_forward
- Treatment of cis-2-bromocyclohexanol with NaOH yields cyclohexanone instead of an epoxide. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism.arrow_forwardTreatment of trans-2-chlorocyclohexanol with NaOH yields 1, 2-epoxy-cyclohexane, but reaction of the cis isomer under the same conditions yields cyclohexanone. Propose mechanisms for both reactions, and explain why the different results are obtained.arrow_forwardDraw out the mechanism for each alkene product. Provide a description of the mechanism of each alkene product below each mechanism drawing. 2-Methylcyclohexanol had three products. These products were 3-methyl-cyclohexene, 1-methyl-cyclohexene, and Methylene-cyclohexanearrow_forward
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