Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 19.20A, Problem 19.28P
Addition of one equivalent of ammonia to 1-bromoheptane gives a mixture of heptan-1-
- a. Give a mechanism to show how this reaction takes place, as far as the dialkylamine.
- b. How would you modify the procedure to get an acceptable yield of heptan-1-amine?
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Chapter 19 Solutions
Organic Chemistry (9th Edition)
Ch. 19.2A - Prob. 19.1PCh. 19.2B - Prob. 19.2PCh. 19.2B - Give correct names for the following amines:Ch. 19.3 - Prob. 19.4PCh. 19.4 - Prob. 19.5PCh. 19.6 - Rank each set of compounds in order of increasing...Ch. 19.8A - Prob. 19.7PCh. 19.8C - Prob. 19.8PCh. 19.8C - Prob. 19.9PCh. 19.8D - a. Show how fragmentation occurs to give the base...
Ch. 19.10B - Propose a mechanism for nitration of pyridine at...Ch. 19.10B - Prob. 19.12PCh. 19.10C - Prob. 19.13PCh. 19.10C - Prob. 19.14PCh. 19.11 - Propose a mechanism to show the individual...Ch. 19.11 - Prob. 19.16PCh. 19.12 - Give the products expected from the following...Ch. 19.13 - Prob. 19.18PCh. 19.13 - Prob. 19.19PCh. 19.14 - Prob. 19.20PCh. 19.15 - Prob. 19.21PCh. 19.15 - Prob. 19.22PCh. 19.16 - Prob. 19.23PCh. 19.17 - Prob. 19.24PCh. 19.17 - Prob. 19.25PCh. 19.18 - Prob. 19.26PCh. 19.19 - Prob. 19.27PCh. 19.20A - Addition of one equivalent of ammonia to...Ch. 19.20A - Prob. 19.29PCh. 19.20B - Show how you would accomplish the following...Ch. 19.20C - Prob. 19.31PCh. 19 - For each compound, 1. classify the...Ch. 19 - Prob. 19.33SPCh. 19 - Within each structure, rank the indicated...Ch. 19 - In each pair of compounds, select the stronger...Ch. 19 - Which of the following compounds are capable of...Ch. 19 - Complete the following proposed acid-base...Ch. 19 - Predict the products of the following reactions:...Ch. 19 - Prob. 19.39SPCh. 19 - Show how m-toluidine can be converted to the...Ch. 19 - The mass spectrum of tert-butylamine follows shows...Ch. 19 - Prob. 19.42SPCh. 19 - The following drugs are synthesized using the...Ch. 19 - Prob. 19.44SPCh. 19 - Synthesize from benzene. (Hint: All of these...Ch. 19 - Propose mechanisms for the following reactions.Ch. 19 - Prob. 19.47SPCh. 19 - Prob. 19.48SPCh. 19 - Prob. 19.49SPCh. 19 - Show how you can synthesize the following...Ch. 19 - Prob. 19.51SPCh. 19 - The alkaloid coniine has been isolated from...Ch. 19 - A chemist is summoned to an abandoned...Ch. 19 - Pyrrole undergoes electrophilic aromatic...Ch. 19 - Prob. 19.55SPCh. 19 - Prob. 19.56SPCh. 19 - An unknown compound shows a weak molecular ion at...Ch. 19 - A compound of formula C11H16N2 gives the IR,...Ch. 19 - (A true story.) A drug user responded to an ad...Ch. 19 - Prob. 19.60SPCh. 19 - Prob. 19.61SPCh. 19 - Prob. 19.62SPCh. 19 - Prob. 19.63SPCh. 19 - Prob. 19.64SPCh. 19 - Prob. 19.65SP
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- 1. Show the products of the reductive amination reactions below; a) Acetone + NH3, followed by H2/Ni2 b) Acetone + CH3NH2, followed by LIBH3CN c) Acetone + (CH3)2NH, followed by LIBH3CN 2. Write the reaction and the names of the products formed in the reaction of aniline and N-methylaniline with: a) NaNO3+HCI followed by CuClI b) NaNO3+HCI followed by Cu20, Cu2*, H20arrow_forwardSelect the best answer. Briefly explain the selection. A mechanism is an acceptable explanation.arrow_forward13arrow_forward
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- Identify each solvent as either protic or aprotic. N-ethylethanamine (diethylamine) Dimethylsulfoxide (DMSO) 1. Protic M hanol 2. Aprotic Tetrahydrofuran (THF) Ethoxyethane (diethyl ether)arrow_forwardWhich reagents are best used to produce 4-methyl-2-pentanol from a ketone? a. amins and trace acid, followed separetely H2/PD/C b. sodium cyanide followed by HCl c. sodium borohydridd followed by acidic work up d. hydrogen cyanide followed by HCl e. none of the abovearrow_forward1. Propose a mechanism and predict the product.arrow_forward
- 4. Please give the starting materials that would be necessary to make the following imines and enamines. a C d N. N atarrow_forwardWhich of those would be formed? Then If the product of the reaction in the previous problem was subsequently mixed with sodium cyanoborohydride, which of the following would result? a. primary alcoholb. secondary alcohol c. primary amined. secondary amine e. tertiary aminearrow_forwardCan you help me understand the two pathways for epoxide and its mechanism?arrow_forward
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