Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 8, Problem 15PP
Practice Problem 8.15
Write a mechanism to explain the following reaction.
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O PRACTICE PROBLEM 8.14
Starting with any needed alkene (or cycloalkene) and assuming you have deuterioace-
tic acid (CH3CO,D) available, outline syntheses of the following deuterium-labeled
compounds.s el en
olad lo nohibbs ad
CH3
(a) (CH3)2CHCH2CH,D
(b) (CH3),CHCHDCH3 (c)
(+ enantiomer)
(d) Assuming you also have available BD3:THF and CH3CO2T, can you suggest a
synthesis of the following?
hab erl
(+ enantiomer)he
imo
(nwond-ben)
CH3
H.
(asoholea)
Problems
8.29 Give the mechanistic symbols (SN1, SN2, E1, E2) that are most consistent with each of the
following statements:
(a) Methyl halides react with sodium ethoxide in ethanol only by this mechanism.
(b) Unhindered primary halides react with sodium ethoxide in ethanol mainly by this
mechanism.
(c) When cyclohexyl bromide is treated with sodium ethoxide in ethanol, the major prod-
uct is formed by this mechanism.
(d) The substitution product obtained by solvolysis of tert-butyl bromide in ethanol arises
by this mechanism.
(e) In ethanol that contains sodium ethoxide, tert-butyl bromide reacts mainly by this
mechanism.
(f) These reaction mechanisms represent concerted processes.
(g) Reactions proceeding by these mechanisms are stereospecific.
(h) These reaction mechanisms involve carbocation intermediates.
(i) These reaction mechanisms are the ones most likely to have been involved when the
products are found to have a different carbon skeleton from the substrate.
(j) Alkyl…
8.30 Outline an efficient synthesis of each of the following compounds from the indicated start-
ing material and any necessary organic or inorganic reagents:
(a) Cyclopentyl cyanide from cyclopentane
(b) Cyclopentyl cyanide from cyclopentene
(c) Cyclopentyl cyanide from cyclopentanol
(d) NCCH₂CH₂CN from ethyl alcohol
(e) Isobutyl iodide from isobutyl chloride
(f) Isobutyl iodide from tert-butyl chloride
(g) Isopropyl azide from isopropyl alcohol
(h) Isopropyl azide from 1-propanol
(i) (S)-sec-Butyl azide from (R)-sec-butyl alcohol
(i) (S)-CH3CH₂CHCH3 from (R)-sec-butyl alcohol
SH
Chapter 8 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
Ch. 8 - Prob. 1PPCh. 8 - Prob. 2PPCh. 8 - Practice Problem 8.3 Provide mechanistic...Ch. 8 - Prob. 4PPCh. 8 - Prob. 5PPCh. 8 - Prob. 6PPCh. 8 - Prob. 7PPCh. 8 - Prob. 8PPCh. 8 - Prob. 9PPCh. 8 - Prob. 10PP
Ch. 8 - Prob. 11PPCh. 8 - Prob. 12PPCh. 8 - Practice Problem 8.13
Specify the appropriate...Ch. 8 - Prob. 14PPCh. 8 - Practice Problem 8.15 Write a mechanism to explain...Ch. 8 - Prob. 16PPCh. 8 - Prob. 17PPCh. 8 - Prob. 18PPCh. 8 - Practice Problem 8.19 Treating cyclohexene with l,...Ch. 8 - Prob. 20PPCh. 8 - Practice Problem 8.21
Predict the products of the...Ch. 8 - Prob. 22PPCh. 8 - Prob. 23PPCh. 8 - Prob. 24PPCh. 8 - Prob. 25PPCh. 8 - Write structural formulas for the products that...Ch. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - 8.29. Give the structure of the products that you...Ch. 8 - Give the structure of the products you would...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - When 3, 3-dimethyl-2-butanol is neared with...Ch. 8 - Prob. 39PCh. 8 - Prob. 40PCh. 8 - Prob. 41PCh. 8 - Prob. 42PCh. 8 - 8.43. Write a mechanism that explains the...Ch. 8 - 8.44. Write a mechanism for the following...Ch. 8 - Write a mechanism that explains formation of the...Ch. 8 - Prob. 46PCh. 8 - 8.47. Farnesene (below) is a compound found in the...Ch. 8 - Limonene is a compound found in orange oil and...Ch. 8 - Prob. 49PCh. 8 - Synthesize the following compound starting with...Ch. 8 - Predict features of their IR spectra that you...Ch. 8 - Deduce the structures of compounds A, B, and C,...Ch. 8 - Ricinoleic acid, a compound that can be isolated...Ch. 8 - 8.54. There are two dicarboxylic acids with the...Ch. 8 - Prob. 55PCh. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Prob. 58PCh. 8 - 8.59. For each of the following questions, please...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Triethylamine, (C2H5)3N, like all amines, has a...Ch. 8 - (a) Synthesize (3S, 4R)-3,...Ch. 8 - Prob. 2LGPCh. 8 - Prob. 3LGPCh. 8 - Prob. 4LGP
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- • PRACTICE PROBLEM 8.13 Specify the appropriate alkene and reagents for synthesis of each of the following alcohols by hydroboration–oxidation. (a) (c) OH (e) CH3 OH AH OH no mobe OH ( (b) (d) (f) OH HT H3 D OH OH HO OHarrow_forwardProvide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)arrow_forward12.6 (opq) Predict the major product and give the name of the reactionarrow_forward
- 8.30 Outline an efficient synthesis of each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents: (g) Isopropyl azide from isopropyl alcohol (h) Isopropyl azide from 1-propanol (i) (S)-sec-butyl azide from (R)-sec-butyl alcoholarrow_forward4.33 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-Butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol (e) 1-Methylcyclopentanol or cyclohexanol Draw the energy diagrams of an SN1 reaction and an SN2 reaction. Include in your drawing anexample reaction. Identify the rate limiting step and label it as unimolecular or bimolecular.arrow_forward4.2 Propose a mechanism for the following reaction and account for the formation of a racemic mixture. H3O+ HOarrow_forward
- • PRACTICE PROBLEM 8.12 Treating a hindered alkene such as 2-methyl-2-butene with BH3:THE leads to the for- mation of a dialkylborane instead of a trialkylborane. When 2 mol of 2-methyl-2-butene is added to 1 mol of BH3, the product formed is bis(3-methyl-2-butyl)borane, nicknamed in reagent "disiamylborane." Write its structure. Bis(3-methyl-2-butyl)borane is a useful certain syntheses that require a sterically hindered borane. (The name “disiamyl" comes from "disecondary-iso-amyl," a completely unsystematic and unacceptable name. The name "amyl" is an old common name for a five-carbon alkyl group.) donbyarrow_forward• PRACTICE PROBLEM 8.24 A, B, and C are alkynes. Elucidate their structures and that of D using the following reaction roadmap. H2, Pt H,, Pt A (C3H14) (C3H14) IR: 3300 cm (1) O3 (2) HOẠC HO, H2, Pt (C3H12) (C3H16) (1) O3 (2) HOAC hol bian vd beeollot Но. ОН AOHarrow_forward8.23 In each of the following indicate which reaction will occur faster. Explain your reasoning. (D) Solvolysis of 1-bromo-2,2-dimethylpropane or tert-butyl bromide in ethanol (E) Solvolysis of isobutyl bromide or sec-butyl bromide in aqueous formic acid (F) Reaction of 1-chlorobutane with sodium acetate in acetic acid or with sodium methoxide in methanolarrow_forward
- 5.34 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol dovolonentanol or cyclohexanolarrow_forwardPredict the reagents for reactions A and B.arrow_forwarddon't know Which of the following, when reacted with HCl, would result in the formation of the same major product at both low and high temperatures? (a) (b)arrow_forward
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