ORGANIC CHEMISTRY-ETEXT REG ACCESS
12th Edition
ISBN: 9781119308362
Author: Solomons
Publisher: WILEY
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Textbook Question
Chapter 7, Problem 62P
(a) Using reactions studied in this chapter, show steps by which this
(b) Could the homologous products obtained in these two cases be relied upon to show infrared absorption in the
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The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formulaC5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.
As reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?
(c) You conducted an experiment involving a hydrohalogenation reaction with starting material A and
HBr. Product C was obtained as the major product of the reaction instead of the regioisomer product
B which you expected.
CH3
CH3
CH3
Br
Br
+ HBr
Product B
Starting material A
Product C
(i) Suggest a detailed reaction mechanism to explain the formation of the major product C.
(ii) Briefly explain why this unexpected major product C predominated in your reaction.
Question 1 Continued
(iii) 1,2-elimination of HBr from product C yields a mixture of two alkenes. Draw the structures of
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Chapter 7 Solutions
ORGANIC CHEMISTRY-ETEXT REG ACCESS
Ch. 7 - Prob. 1PPCh. 7 - Prob. 2PPCh. 7 - Prob. 3PPCh. 7 - Prob. 4PPCh. 7 - Practice Problem 7.5
How many stereoisomers are...Ch. 7 - Prob. 6PPCh. 7 - Prob. 7PPCh. 7 - PRACTICE PROBLEM 7.8
Examine Solved Problem 7.3....Ch. 7 - Prob. 9PPCh. 7 - Practice Problem 7.10 When...
Ch. 7 - Practice Problem 7.11
(a) When...Ch. 7 - Prob. 12PPCh. 7 - Prob. 13PPCh. 7 - Practice Problem 7.14
Dehydration of 2-propanol...Ch. 7 - Practice Problem 7.15
Rank the following alcohols...Ch. 7 - Practice Problem 7.16
Acid-catalyzed dehydration...Ch. 7 - Practice Problem 7.17 Acid-catalyzed dehydration...Ch. 7 - Prob. 18PPCh. 7 - Prob. 19PPCh. 7 - Practice Problem 7.20
Show how you might...Ch. 7 - Prob. 21PPCh. 7 - Prob. 22PPCh. 7 - Practice Problem 7.23
Write the structure of...Ch. 7 - Prob. 24PPCh. 7 - Prob. 25PPCh. 7 - Practice Problem 7.26 (a) Devise retrosynthetic...Ch. 7 - Each of the following names is incorrect, Give the...Ch. 7 - Prob. 28PCh. 7 - Prob. 29PCh. 7 - Give the IUPAC names for each of the following:...Ch. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - 7.35. Write structural formulas for all the...Ch. 7 - 7.36. Explain the following observations: When...Ch. 7 - Prob. 37PCh. 7 - Arrange the following alcohols in order of their...Ch. 7 - Prob. 39PPCh. 7 - Prob. 40PPCh. 7 - Prob. 41PPCh. 7 - Prob. 42PPCh. 7 - Your task is to prepare isopropyl methyl ether by...Ch. 7 - Prob. 44PCh. 7 - Prob. 45PCh. 7 - Prob. 46PCh. 7 - 7.47. Starting with an appropriate alkyl halide...Ch. 7 - Prob. 48PCh. 7 - 7.49. What is the index of hydrogen deficiency...Ch. 7 - Prob. 50PCh. 7 - Prob. 51PCh. 7 - Compounds I and J both have the molecular formula...Ch. 7 - Prob. 53PCh. 7 - 7.54. Outline a synthesis of phenylethyne from...Ch. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - cis-4-Bromocyclohexanol tBuOHtBuO racemic C6H10O...Ch. 7 - Prob. 59PPCh. 7 - Consider the interconversion of cis-2-butene and...Ch. 7 - Prob. 61PCh. 7 - (a) Using reactions studied in this chapter, show...Ch. 7 - Prob. 63PCh. 7 - Prob. 64PCh. 7 - 1. Write the structure(s) of the major product(s)...Ch. 7 - Prob. 2LGPCh. 7 - (a) Write the structure of the product(s) formed...Ch. 7 - Prob. 4LGP
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- The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.arrow_forward(3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)arrow_forwardGive the reaction mechanism showing all possible products for the following reactions: (a) Reaction of 1-propene with hydrogen bromide, HBr (9) (b) Reaction of ethene with bromine, Br2 (1)arrow_forward
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