Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Question
Chapter 22.14, Problem 15P
Interpretation Introduction
Interpretation:
The synthesis of the given compounds by using aniline as a starting material is to be determined.
Concept Introduction:
The replacement or substitution of one
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Suggest a synthesis for the following compound from the indicated starting materials and any other necessary organic and inorganic materials:
from
&
19.60 Draw the major organic products for each of the following reactions.
(a)
(b)
OEt
LOCH3
Pd(PPH3)4, NaOH
EtO
Pd(PPh)4, NaOH
-?
THE
THE
(c)
(d)
Pd(OAc)2
Pd(OAc)2.
?
PPH3,EtgN
?
PPH3,EtgN
Br
HN
21.10 Suggest reagents.
HN
Chapter 22 Solutions
Organic Chemistry - Standalone book
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.4 - Prob. 5PCh. 22.4 - Prob. 6PCh. 22.4 - Prob. 7PCh. 22.4 - Prob. 8PCh. 22.4 - Prob. 9PCh. 22.7 - Prob. 10P
Ch. 22.8 - Problem 22.11 Three of the following amines can be...Ch. 22.9 - Prob. 12PCh. 22.10 - Prob. 13PCh. 22.13 - Prob. 14PCh. 22.14 - Prob. 15PCh. 22.15 - Prob. 16PCh. 22.15 - Prob. 17PCh. 22.17 - Prob. 18PCh. 22.17 - Prob. 19PCh. 22.17 - Prob. 20PCh. 22.17 - Prob. 21PCh. 22.18 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Arrange the following compounds or anions in each...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - The compound shown is a somewhat stronger base...Ch. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Write the structure of the product formed on...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - Devise efficient syntheses of each of the...Ch. 22 - Prob. 46PCh. 22 - Prob. 47PCh. 22 - Prob. 48PCh. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - Prob. 52PCh. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56DSPCh. 22 - Prob. 57DSPCh. 22 - Prob. 58DSPCh. 22 - Prob. 59DSPCh. 22 - Synthetic Applications of Enamines The formation...Ch. 22 - Prob. 61DSP
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- Propose a reasonable synthesis of the following reaction:.arrow_forward18.18 Provide a structural formula for the product from each of the following reactions. (a) (c) (e (1) LDA (2) CH,CH,I NaH CI (b) (d) O. (f Br, CH,CO,H Br, (excess), NaOHarrow_forwardMeO 22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an acetoacetic ester synthesis (Section 19.6). 5 3 6 CH₂O CI acetoacetic ester synthesis HC 7 MeO MeO 1 8 2-Methoxynaphthalene Nabumetone (a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at carbon 5 or 7. (b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum- etone is completed.arrow_forward
- Rank the following compounds in order of increasing basicity in aqueous solution, least basic first a) Propylamine, ammonium, dipropylamine b) Methyl-3-aminopropanoate, sectutylamine, NH3*CH2CH2NH2 c) Aniline, methyl m-aminobenzoate,, methy! p-aminobenzoatearrow_forward22.39 Propose an efficient synthesis for each of the following compounds using the acetoacetic ester synthesis: ... 4.70. (a) (b) (c) (d)arrow_forwardArrange the following compounds in order of decreasing acidity and explain why?arrow_forward
- Rank the following compounds in order of increasing acidity and explain in detail your choice of order.arrow_forwardOctinoxate is an unsaturated ester used as an active ingredient in sunscreens. (a) What carbonyl compounds are needed to synthesize this compound using a condensation reaction? (b) Devise a synthesis of octinoxate from the given organic starting materials and any other needed reagents.arrow_forwardSafrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4- methylenedioxymethamphetamine, “Ecstasy”) by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine.arrow_forward
- Safrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4-methylenedioxymethamphetamine, "Ecstasy") by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine. NHCH9 MDMA safrolearrow_forwardCompound A has acidity stronger than compound Barrow_forward18.26 Synthesize each of the following compounds from diethyl malonate or ethyl acetoacetate and any other organic and inorganic reagents. (a) (c) (e) OH (b) OH (d) (f)arrow_forward
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