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 20, Problem 28P
What products would you expect to be formed when each of the
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1. Which of the following amines would make an imine if reacted with an aldehyde or ketone?
A
B
e. Which of the following moleculo
C
NH₂
AN
D
2) Which of the following amine gives more faster addition and substitution reaction with the following carbonyl
compounds? Write the structures of the products in boxes.
NH2
CI
NH2
Provide the steps to convert the following aldehyde to the given amine product.
Chapter 20 Solutions
Organic Chemistry
Ch. 20 - Prob. 1PPCh. 20 - Prob. 2PPCh. 20 - Practice Problem 20.3
Write a mechanism that...Ch. 20 - Prob. 4PPCh. 20 - PRACTICE PROBLEM 20.5 Outline a preparation of...Ch. 20 - Prob. 6PPCh. 20 - Prob. 7PPCh. 20 - Prob. 8PPCh. 20 - Prob. 9PPCh. 20 - Prob. 10PP
Ch. 20 - Practice Problem 20.11 In the preceding examples...Ch. 20 - Prob. 12PPCh. 20 - Prob. 13PPCh. 20 - Practice Problem 20.14
Outline a synthesis of...Ch. 20 - Prob. 15PPCh. 20 - Prob. 16PPCh. 20 - Prob. 17PPCh. 20 - Prob. 18PPCh. 20 - Prob. 19PCh. 20 - 20.20 Give common or systematic names for each of...Ch. 20 - Which is the most basic nitrogen in each compound?...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Show how you might synthesize each of the...Ch. 20 - Prob. 25PCh. 20 - 20.26 Provide the major organic product from each...Ch. 20 - Prob. 27PCh. 20 - 20.28 What products would you expect to be formed...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Prob. 31PCh. 20 - Write equations for simple chemical rests or state...Ch. 20 - Prob. 33PCh. 20 - Explain the following, including mention of key...Ch. 20 - 20.35 Provide a detailed mechanism for each of the...Ch. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - 20.40 Give structures for compounds R-W:
Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Diethylpropion (shown here) is a compound used in...Ch. 20 - Prob. 44PCh. 20 - 20.45 Compound W is soluble in dilute aqueous HCI...Ch. 20 - 20.46 Propose structures for compounds X, Y, and...Ch. 20 - Compound A(C10H15N) is soluble in dilute HCI. The...Ch. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - For each of the following, identify the product...Ch. 20 - 20.51 Develop a synthesis for the following...Ch. 20 - 20.52 When phenyl isochiocyanatc, , is reduced...Ch. 20 - Prob. 53PCh. 20 - 20.54 Propose a mechanism that can explain the...Ch. 20 - When acetone is treated with anhydrous ammonia in...Ch. 20 - Prob. 56P
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- Write the mechanism for the following reactions: 1. the acid-catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine 2. the acid-catalyzed hydrolysis of an enamine to a carbonyl compound and a secondary amine a. How do the two mechanisms differ?arrow_forwardDraw the structure of the product that will be formed when each of the following amines reacts with sodium nitrite and hydrochloric acid, followed by cuprous chloride. (e) p-propylanilinearrow_forwardWhich of these amine will react fastest in a reductive amination reaction?arrow_forward
- Account for the experimental behavior of each class of amines (primary,secondary and tertiary) based on their relative reactivities with benzenesulfonyl chloride.arrow_forwardWhich of the following functional groups will react faster and at lower conditions to a nucleophilic attack? (you can think of a nucleophilic attack by an amine). O a. Carboxylic Acid o b. Nitrile о с. Асyl Нalide d. Esterarrow_forwardAn aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is tertiary, an amide is not formed. What product is formed? Explain.arrow_forward
- a) What are the difficulties with the following reaction to synthesize an amine. + HBr Br + NH3 NH2 b) Show a possible alternatives to this synthesis.arrow_forwardOut of acid chlorides (least stable), anhydrides, esters, and amides (most stable). True or false Acid chlorides would be the most reactive to hydrolysis and Amides would be the least reactivearrow_forwardWhy is there a need to add two (2) equivalents of amine in the reaction of an acid chloride and an amine ? A) The extra amine will deprotonate the amine or alcohol, making it a better nucleophile. B) The extra amine will neutralize the acid by-product of the reaction. C) The extra amine will protonate the carbonyl of the acid chloride, making it more reactive. D) The extra amine will absorb the heat of the reaction.arrow_forward
- Which of the following statements about carbonyl derivatives is FALSE? O Formation of an amide from an acyl chloride requires use of two equivalents of the amine. O The product of the base-promoted saponification of an ester is a carboxylate anion. O Acetals are great protecting groups for aldehydes and ketones because they are stable to acidic conditions. O Despite being a terrible leaving group, H2N¯ is indeed the leaving group in the base-promoted hydrolysis of an amide. O Transesterification can occur under either acidic or basic reactions conditions.arrow_forwardthis drug contains one or more building blocks derived from either ethylene oxide or epichlorohydrin.Identify the part of each molecule that can be derived from one or the other of the building block and propose structural formulas for the nucleophile(s) that can be used along with either ethylene oxide or epichlorohydrin to synthesize each molecule.arrow_forwardDraw the possible stereoisomers of 2-methylocta-4,6-dien-1-amine. Note that E-, Z- isomers of each stereoisomer are also possible and would not be accounted for by the formula above; draw any E- or Z- isomers.arrow_forward
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