Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 19, Problem 18PP
Practice Problem 19.18
What experimental conditions would favor the cyclization process in an intramolecular aldol reaction over intermolecular condensation?
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What reactant can be used to make this compound by an intramolecular aldol reaction?
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(B)
(C)
(D)
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The following intermediate was needed for the synthesis of tamoxifen, a widely used
antiestrogen drug for treating estrogen-dependent cancers such as breast and ovarian
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Needed for the
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Practice Problem 19.54
Z Your answer is partially correct. Try again.
Predict the major product(s) (A - K) from the treatment of acetone with the following compounds (a-c):
NH2
HO
Eto
OEt
A:
B:
C:
D:
E:
F:
OH
OH
но
CN
G:
H:
I:
J:
(a) [H*], excess EtOH, (-H20)
Major Product(s):
(ь) NaBH4, Meон
B
Major Product(s):
(c) LAH followed by H20
Major Product(s):
SHOW HINT
Chapter 19 Solutions
Organic Chemistry
Ch. 19 - PRACTICE PROBLEM 19.1 (a) Write a mechanism. for...Ch. 19 - Practice Problem 19.2
Since the products obtained...Ch. 19 - Prob. 3PPCh. 19 - PRACTICE PROBLEM 19.4
Write mechanisms that...Ch. 19 - Prob. 5PPCh. 19 - Prob. 6PPCh. 19 - Practice Problem 19.7 The acid-catalyzed aldol...Ch. 19 - Prob. 8PPCh. 19 - Practice Problem 19.9
(a) Provide a mechanism for...Ch. 19 - Prob. 10PP
Ch. 19 - Practice Problem 19.11 Outlined below is a...Ch. 19 - Prob. 12PPCh. 19 - Prob. 13PPCh. 19 - Prob. 14PPCh. 19 - Practice Problem 19.15
Starting with ketones and...Ch. 19 - Practice Problem 19.16 Assuming that dehydration...Ch. 19 - Practice Problem 19.17 What starting compound...Ch. 19 - Practice Problem 19.18
What experimental...Ch. 19 - Prob. 19PPCh. 19 - Practice Problem 19.20
When acrolein (propenal)...Ch. 19 - Prob. 21PPCh. 19 - PRACTICE PROBLEM 19.22
Qutline reasonable...Ch. 19 - Prob. 23PCh. 19 - Show all steps in the following syntheses. You may...Ch. 19 - Prob. 25PCh. 19 - Prob. 26PCh. 19 - Prob. 27PCh. 19 - 19.28 Show how the diketone at the right could be...Ch. 19 - Prob. 29PCh. 19 - 19.30 Write a detailed mechanism for the following...Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - 19.33 Predict the products from each of the...Ch. 19 - Prob. 34PCh. 19 - Show how each of the following transformations...Ch. 19 - Prob. 36PCh. 19 - What reagents would you use to bring about each...Ch. 19 - Prob. 38PCh. 19 - Prob. 39PCh. 19 - 19.40 When the aldol reaction of acetaldehyde is...Ch. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - 19.43 The following reaction illustrates the...Ch. 19 - What is the structure of the cyclic compound that...Ch. 19 - Prob. 45PCh. 19 - Prob. 46PCh. 19 - Prob. 47PCh. 19 - Predict the products from the following reactions....Ch. 19 - Prob. 49PCh. 19 - Prob. 50PCh. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - The Perkin condensation is an aldol-type...Ch. 19 - 19.55 (a) Infrared spectroscopy provides an easy...Ch. 19 - Allowing acetone to react with 2 molar equivalents...Ch. 19 - (+) Fenchone is a terpenoid that can be isolated...Ch. 19 - Prob. 58PCh. 19 - Prob. 59PCh. 19 - 19.60 Develop a synthesis for the following...Ch. 19 - 19.61 Provide a mechanism for each of the...Ch. 19 - 19.62 (a) Deduce the structure of product A,...Ch. 19 - Prob. 63PCh. 19 - Prob. 1LGP
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- Identify the reagents represented by the letters a-e in the following scheme:arrow_forwardThe compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forward) Cinnamaldehyde is used in artificial cinnamon flavoring. Show how cinnamaldehydeis synthesized by a crossed aldol condensation followed by dehydration.arrow_forward
- 19.18 Draw a structural formula for the product of the aldol reaction of each compound by itself and for the a,ß-unsaturated aldehyde or ketone formed from dehydration of each aldol product. If no reaction is expected to occur, denote with "No reaction." 4 (a) (b) H $orar (c) (d) Harrow_forwardWhich of the following are a major product of the reaction sequence shown belo (1) Br2, FeBr3 (2) Mg/ether он он (A) (B) (3) (4) dil H* /H;O (C) (D) он Compound C Compounds B and D OCompounds A and B Compound Darrow_forward• Using aldol or crossed aldol condensation, suggest a synthesis of the following compounds: a b مليمت H3C H3C CH3 H3C ge H Savedarrow_forward
- (iv) The intramolecular aldol reaction of Z and subsequent dehydration gives a,ß-unsaturated ketone AA. Draw the structure of AA and provide detailed reaction mechanisms for the transformation. N NaOH EtOH AAarrow_forward(b) Give both the structures and IUPAC names of the reactants for the compound below formed via a crossed aldol reaction with KOH as promotor. Explain why only one product is formed:arrow_forwardWe have seen that the alpha carbon atom of an enamine can function as a nucleophile in a Michael reaction, and in fact, enamines can function as nucleophiles in a wide variety of reactions. For example, an enamine will undergo alkylation when treated with an alkyl halide. Draw the structure of intermediate A and the alkylation product B in the following reaction scheme (J. Am. Chem. Soc. 1954, 76, 2029-2030): TSOH -H₂O NH A 1) CHgI 2) H₂O+ B + NH Modify the given copy of the starting material to draw compound A. If needed, use the single bond tool to interconvert between double and single bonds. Edit Drawingarrow_forward
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