EBK ORGANIC CHEMISTRY STUDY GUIDE AND S
6th Edition
ISBN: 9781319385415
Author: PARISE
Publisher: VST
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Chapter 7, Problem 7.46AP
Interpretation Introduction
(a)
Interpretation:
The structure and stereochemistry of the expected products for the addition of
Concept introduction:
Stereochemistry is the study of the arrangement of the atoms and molecules in the space and its effects on the reactions.
The addition reactions on the
Interpretation Introduction
(b)
Interpretation:
The structure and stereochemistry of the expected products for the reaction of cyclopentene with
Concept introduction:
Stereochemistry is the study of the arrangement of the atoms and molecules in the space and its effects on the reactions.
The addition reactions on the alkenes are very common as there is electron density available on the alkene due to double bond electron-cloud.
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Write the structure of the major organic product formed in the reaction of each of the following with hydrogen bromide in the absence of peroxides and in their presence. (a) 1-Pentene (b) 2-Methyl-2-butene (c) 1-Methylcyclohexene
1. Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C8H12.
(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC—(CH2)6—COOH. Draw the structure of W.
(b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethyl sulfide, gives two equivalents of butanedial,
O=CH—CH2CH2—CH=O. Draw the structure of X.
Acid-catalyzed dehydration of 2,2-dimethyl-1-hexanol gave a number of isomeric alkenes including 2-methyl-2-heptene as shown in the following equation.(a) Write a stepwise mechanism for the formation of 2-methyl-2-heptene, using curved arrows to show the flow of electrons. (b) What other alkenes do you think are formed in this reaction?
Chapter 7 Solutions
EBK ORGANIC CHEMISTRY STUDY GUIDE AND S
Ch. 7 - Prob. 7.1PCh. 7 - Prob. 7.2PCh. 7 - Prob. 7.3PCh. 7 - Prob. 7.4PCh. 7 - Prob. 7.5PCh. 7 - Prob. 7.6PCh. 7 - Prob. 7.7PCh. 7 - Prob. 7.8PCh. 7 - Prob. 7.9PCh. 7 - Prob. 7.10P
Ch. 7 - Prob. 7.11PCh. 7 - Prob. 7.12PCh. 7 - Prob. 7.13PCh. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Prob. 7.16PCh. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Prob. 7.20PCh. 7 - Prob. 7.21PCh. 7 - Prob. 7.22PCh. 7 - Prob. 7.23PCh. 7 - Prob. 7.24PCh. 7 - Prob. 7.25PCh. 7 - Prob. 7.26PCh. 7 - Prob. 7.27PCh. 7 - Prob. 7.28PCh. 7 - Prob. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Prob. 7.31PCh. 7 - Prob. 7.32PCh. 7 - Prob. 7.33PCh. 7 - Prob. 7.34APCh. 7 - Prob. 7.35APCh. 7 - Prob. 7.36APCh. 7 - Prob. 7.37APCh. 7 - Prob. 7.38APCh. 7 - Prob. 7.39APCh. 7 - Prob. 7.40APCh. 7 - Prob. 7.41APCh. 7 - Prob. 7.42APCh. 7 - Prob. 7.43APCh. 7 - Prob. 7.44APCh. 7 - Prob. 7.45APCh. 7 - Prob. 7.46APCh. 7 - Prob. 7.47APCh. 7 - Prob. 7.48APCh. 7 - Prob. 7.49APCh. 7 - Prob. 7.50APCh. 7 - Prob. 7.51APCh. 7 - Prob. 7.52APCh. 7 - Prob. 7.53APCh. 7 - Prob. 7.54APCh. 7 - Prob. 7.55APCh. 7 - Prob. 7.56APCh. 7 - Prob. 7.57APCh. 7 - Prob. 7.58APCh. 7 - Prob. 7.59APCh. 7 - Prob. 7.60APCh. 7 - Prob. 7.61APCh. 7 - Prob. 7.62APCh. 7 - Prob. 7.63APCh. 7 - Prob. 7.64APCh. 7 - Prob. 7.65APCh. 7 - Prob. 7.66APCh. 7 - Prob. 7.67APCh. 7 - Prob. 7.68APCh. 7 - Prob. 7.69APCh. 7 - Prob. 7.70APCh. 7 - Prob. 7.71APCh. 7 - Prob. 7.72APCh. 7 - Prob. 7.73APCh. 7 - Prob. 7.74APCh. 7 - Prob. 7.75AP
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- Give the structure, exclusive of stereochemistry, of the principal organic product formed on reaction of 2,3-dimethyl-1,3-butadiene with each of the following:(a) 2 mol H2, platinum catalyst(b) 1 mol HCl (product of 1,2-addition)(c) 1 mol HCl (product of 1,4-addition)(d) 1 mol Br2 (product of 1,2-addition)(e) 1 mol Br2 (product of 1,4-addition)(f) 2 mol Br2arrow_forward3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) dimethyl sulfoxide (DMSO) is used in place of methanol (b) methanol is used by itself without sodium methoxide (c) 1-chloro-2,2,-dimethylpropane is used in place of 3-chloro-2-methylpropenearrow_forwardChlorination of 2-butanone yields two isomeric products, each having the molecular formula C4H7ClO. (a) What are these two compounds? (b) Write structural formulas for the enol intermediates that lead to each of these compounds. (c) Using curved arrows, show the flow of electrons in the reaction of each of the enols with Cl2.arrow_forward
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- Compound D undergoes a reaction with hydrogen bromide, HBr to produce 2-bromobutane. D exists as cis-trans isomers and decolourises bromine solution in methylene chloride, CH2Cl2. (i) Draw and name the structure of compound D. (ii) Draw two (2) constitutional isomers of compound D.arrow_forwardWhich of the following is true for the reactions of alkyl halides? (a) The characteristic reactions of alkyl halides are oxidation and reduction.(b) The characteristic reactions of alkyl halides are elimination and substitutionc. The characteristic reactions of alkyl halides are addition and substitutiond. Characteristic reactions of alkyl halides are addition and elimination.arrow_forwardWrite the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide (CH3)2Sarrow_forward
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