Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 10.10, Problem 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.
Treating cyclohexene with HBr in the presence of acetic acid gives bromocyclohexane
(85%) and cyclohexyl acetate (15%).
Br
OCCH
CH,COH
+ HBr
Bromocyclohexane Cyclohexyl acetate
(15%)
Cyclohexene
(85%)
Propose a mechanism for the formation of the latter product.
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.
Chapter 10 Solutions
Organic Chemistry (6th Edition)
Ch. 10.1 - Prob. 1PCh. 10.2 - Problem 10.2 How many degrees of unsaturation are...Ch. 10.3 - Give the IUPAC name for each alkene. abcdeCh. 10.3 - Give the IUPAC name for each polyfunctional...Ch. 10.3 - Prob. 9PCh. 10.6 - Linolenic acidTable 10.2 and stearidonic acid are...Ch. 10.7 - Prob. 12PCh. 10.9 - Problem 10.13 What product is formed when each...Ch. 10.9 - Prob. 14PCh. 10.10 - Problem 10.15 Draw the products formed when each...
Ch. 10.10 - Prob. 16PCh. 10.10 - Prob. 17PCh. 10.10 - Addition of HBr to which of the following alkenes...Ch. 10.11 - Problem 10.19 Draw the products, including...Ch. 10.11 - Prob. 20PCh. 10.12 - Problem 10.21 What two alkenes give rise to each...Ch. 10.12 - Prob. 22PCh. 10.13 - Problem 10.23 Draw the products of each reaction,...Ch. 10.14 - Problem 10.24 Draw all stereoisomers formed in...Ch. 10.15 - Prob. 25PCh. 10.16 - Problem 10.26 What alkylborane is formed from...Ch. 10.16 - Draw the products formed when each alkene is...Ch. 10.16 - What alkene can be used to prepare each alcohol as...Ch. 10.16 - Prob. 29PCh. 10.17 - Draw the products of each reaction using the two...Ch. 10.18 - 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. 34PCh. 10 - 10.35 Calculate the number of degrees of...Ch. 10 - Prob. 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. 39PCh. 10 - 10.40 (a) Draw all possible stereoisomers of, and...Ch. 10 - Prob. 41PCh. 10 - 10.42 Now that you have learned how to name...Ch. 10 - Prob. 43PCh. 10 - Prob. 44PCh. 10 - Prob. 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. 48PCh. 10 - Draw the constitutional isomer formed in each...Ch. 10 - Prob. 50PCh. 10 - Draw all stereoisomers formed in each reaction. a....Ch. 10 - Draw the products of each reaction, including...Ch. 10 - Prob. 53PCh. 10 - Draw a stepwise mechanism that shows how all three...Ch. 10 - Less stable alkenes can be isomerized to more...Ch. 10 - Prob. 60PCh. 10 - Prob. 61PCh. 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...
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- Acid-catalyzed dehydration of 3-methyl-2-butanol gives three alkenes: 2-methyl-2- butene, 3-methyl-1-butene, and 2-methyl-1-butene. Propose a mechanism to account for the formation of each productarrow_forwardWhen 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.arrow_forwardWhen 1-cyclohexylethanol is treated with concentrated aqueous HBr, the major product is 1-bromo-1-ethylcyclohexane. Propose a mechanism for this reaction.arrow_forward
- Draw the products formed when the following alkynes are treated with each set of reagents: [1] H2O, H2SO4, HgSO4; or [2] R2BH followed by H2O2, −OH.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardWhen cyclohexene is reacted with hydrobromic acid in acetic acid, the major product is bromocyclohexane. There is a small amount of cyclohexyl acetate formed. What is the mechanism that forms both compounds? What is the purification procedure that isolates both compounds?arrow_forward
- Write the expected substitution product(s) for each reaction and predict the mechanism by which each product is formed.arrow_forwardGive a step-by-step mechanism for the following substitution reactions:arrow_forwardExplain the different products of the following two reactions by considering the mechanism by which each reaction proceeds. As part of your explanation, use the curved arrow formalism to draw a mechanism for each reaction. CH,OH CH2=CH-CH-CH, + Na*¯OCH, CH;=CH-CH-CH3 Br OCH, CH,=CH-CH-CH, + CH,OH – CH,=CH–CH–CH, + CH,CH=CHCH, Br OCH, OCH,arrow_forward
- $ 2,6-Di-tert-butyl-4-methylphenol, alternatively known as butylated hydroxytoluene (BHT), is used as an antioxidant in foods to"retard spoilage" ( synthesized industrially from 4-methylphenol by reaction with 2-methylpropene in the presence of phosphoric acid. Propose a mechanism for this reaction. ВНT is OH OH H&PO, 4-Methylphenol 2-Methylpropene (p-Cresol) 2,6-Di-tert-butyl-4-methylphenol "Butylated hydroxytoluene" (BHT)arrow_forwardPropose a series of reactions that will convert the given starting material into the given product. Make sure to draw the product of each successive reaction. For racemic molecules, you only need to draw one enantiomer. Each synthesis can be accomplished in three steps or less. a) methylcyclopentane → 1-methylcyclopentanol b) 4-bromo-1-butanol → 3-buten-1-ol c) bromocyclohexane → trans-1,2-cyclohexanediol (racemic)arrow_forward1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol. Propose a mechanism for this reaction.arrow_forward
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