Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 16, Problem 17PP
Practice Problem 16.17
In addition to triphenylphosphine, assume that you have available as starting materials any necessary
(a)
(b)
(c)
(d)
(e)
(f)
(g)
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Provide the reagents and solvents (where appropriate) needed to bring about the following
transformations.
(a)
CI
(b)
Give the structure of the product formed on reaction of ethyl acetoacetate with each of the following: (a) 1-Bromopentane and sodium ethoxide (b) Saponification (basic hydrolysis) and decarboxylation of the product in part (a) (c) Methyl iodide and the product in part (a) treated with sodium ethoxide (d) Saponification and decarboxylation of the product in part (c) (e) 1-Bromo-3-chloropropane and one equivalent of sodium ethoxide (f) Product in part (e) treated with a second equivalent of sodium ethoxide (g) Saponification and decarboxylation of the product in part (f) (h) Phenyl vinyl ketone and sodium ethoxide (i) Saponification and decarboxylation of the product in part (h)
(c) Answer each of the questions below that relate to acetophenone:
Xo
(i)
(ii)
(iii)
Draw the structure of the enol form of acetophenone.
Give a stepwise mechanism for the conversion of acetophenone into its
enol form.
Show how each of the three compounds A, B and C below can be
prepared from acetophenone. Explain clearly what reactants/reagents
would be required in each case.
odocor
A
B
Br
C
Chapter 16 Solutions
Organic Chemistry
Ch. 16 - PRACTICE PROBLEM 16.1 (a) Give IUPAC substitutive...Ch. 16 - Prob. 2PPCh. 16 - Prob. 3PPCh. 16 - Practice Problem 16.4
Provide the reagents and...Ch. 16 - Prob. 5PPCh. 16 - Prob. 6PPCh. 16 - Prob. 7PPCh. 16 - Prob. 8PPCh. 16 - Prob. 9PPCh. 16 - Practice Problem 16.10
Shown below is the...
Ch. 16 - Prob. 11PPCh. 16 - Practice Problem 16.12
What product would be...Ch. 16 - Prob. 13PPCh. 16 - Practice Problem 16.14
Dihydropyran reacts readily...Ch. 16 - Practice Problem 16.15 Show how you might use...Ch. 16 - Practice Problem 16.16 (a) Show how you might...Ch. 16 - Practice Problem 16.17
In addition to...Ch. 16 - Practice Problem 16.18
Triphenylphosphine can be...Ch. 16 - Prob. 19PPCh. 16 - PRACTICE PROBLEM 16.20
Give the structure of the...Ch. 16 - PRACTICE PROBLEM 16.21 What would be the major...Ch. 16 - Prob. 22PCh. 16 - 16.23 Write structural formulas for the products...Ch. 16 - Give structural formulas for the products formed...Ch. 16 - 16.25 What products would be obtained when...Ch. 16 - Predict the major organic product from each of the...Ch. 16 - 16.27 Predict the major product from each of the...Ch. 16 - 16.28 Predict the major product from each of the...Ch. 16 - Prob. 29PCh. 16 - 16.30 Write detailed mechanisms for each of the...Ch. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Show how you would convert benzaldehyde into each...Ch. 16 - 16.34 Show how ethyl phenyl ketone could be...Ch. 16 - Show how benzaldehyde could be synthesized from...Ch. 16 - Give structures for compounds AE. Cyclohexanol...Ch. 16 - Prob. 37PCh. 16 - Prob. 38PCh. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41PCh. 16 - Prob. 42PCh. 16 - 16.43 The structure of the sex pheromone...Ch. 16 - Provide reagents that would accomplish each of the...Ch. 16 - Write a detailed mechanism for the following...Ch. 16 - Prob. 46PCh. 16 - Dutch elm disease is caused by a fungus...Ch. 16 - Prob. 48PCh. 16 - Compounds W and X are isomers; they have the...Ch. 16 - Compounds Y and Z are isomers with the molecular...Ch. 16 - Compound A (C9H18O) forms a phenylhydrazone, but...Ch. 16 - Compound B (C8H12O2) shows a strong carbonyl...Ch. 16 - Prob. 53PCh. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - (a) What would be the frequencies of the two...Ch. 16 - Prob. 57PCh. 16 - Prob. LGP
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- Rank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forwardShow how you might synthesize the following compounds, using acetylene and anysuitable alkyl halides as your starting materials. If the compound given cannot besynthesized by this method, explain why.(a) hex-1-ynearrow_forwardProvide the reagents required to complete the following transformations. (a) □ (b) на öd io: HỌ: 0.arrow_forward
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