Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 17.10, Problem 35P
Excess ammonia must be used when a primary
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When trichloroacetaldehyde is dissolved in water, almost all of it is converted to the hydrate. Chloral hydrate, the product of the reaction, is a sedative that can be lethal. A cocktail laced with it is known—in detective novels,at least—as a “Mickey Finn.” Explain why an aqueous solution of trichloroacetaldehyde is almost all hydrate.
When trichloroacetaldehyde is dissolved in water, almost all of it is converted to the hydrate. Chloral hydrate, the product of the reaction, is a sedative that can be lethal. A cocktail laced with it is known—in detective novels, at least—as a “Mickey Finn.” Explain why an aqueous solution of trichloroacetaldehyde is almost all hydrate.
C) a nitrile
D) an amine nitrite salt
DIRECTIONS: Each of the following questions
or incomplete statements below is followed by four
suggested answers lettered A - D. Select or
choose the letters of the best answer to the
question or incomplete statement.
7. An organic nitrogen compound, X, gives
ammonia on warming with dilute aqueous
sodium hydroxide, X could be
A) ethanamide B) ethylamine
C) phenylamine D) amino ethanoic acid
Which one of the following reagents reacts
1.
in a similar fashion with both phenylamine
(C H,NH,) and ethylamine.
A) Br,(aq)
C) conc. HNO, D) cold HNO (aq)
2. Phenylamine (aniline) can be prepared by
reducing nitrobenzene with tin and
concerntrated hydrochloric acid followed by
the addition of alkali and finally steam
distillation. The alkali is added to;
A) prevent oxidation of phenylamine.
B) liberate free phenylamine from solution
C) dissolve excess nitro benzene
D) dissolve the phenylamine
8. Arrange the following molecules in their
increasing order of base…
Chapter 17 Solutions
Organic Chemistry
Ch. 17.1 - Prob. 1PCh. 17.1 - Give two names for each of the following:Ch. 17.1 - Name the following:Ch. 17.2 - Prob. 4PCh. 17.4 - What products are formed when the following...Ch. 17.4 - We saw on the previous page that...Ch. 17.4 - a. How many stereoisomers are obtained from the...Ch. 17.4 - Prob. 9PCh. 17.4 - Write the mechanism for the reaction of acetyl...Ch. 17.4 - Prob. 11P
Ch. 17.4 - Show how the following compounds can be...Ch. 17.5 - Prob. 13PCh. 17.5 - Prob. 14PCh. 17.6 - In the mechanism for cyanohydrin formation, why is...Ch. 17.6 - Prob. 16PCh. 17.6 - Prob. 17PCh. 17.6 - Show two ways to convert an alkyl halide into a...Ch. 17.7 - Prob. 20PCh. 17.7 - Prob. 21PCh. 17.7 - Prob. 22PCh. 17.7 - Prob. 23PCh. 17.8 - Prob. 24PCh. 17.9 - What reducing agents should be used to obtain the...Ch. 17.9 - Prob. 26PCh. 17.9 - Prob. 27PCh. 17.10 - Prob. 28PCh. 17.10 - Prob. 29PCh. 17.10 - Prob. 30PCh. 17.10 - The pKa of protonated acetone is about 7.5. and...Ch. 17.10 - Prob. 32PCh. 17.10 - Prob. 33PCh. 17.10 - Prob. 34PCh. 17.10 - Excess ammonia must be used when a primary amine...Ch. 17.10 - The compounds commonly known as amino acids are...Ch. 17.11 - Hydration of an aldehyde is also catalyzed by...Ch. 17.11 - Which ketone forms the most hydrate in an aqueous...Ch. 17.11 - When trichloroacetaldehyde is dissolved in water,...Ch. 17.12 - Which of the following are a. hermiacetals? b....Ch. 17.12 - Prob. 41PCh. 17.12 - Explain why an acetal can be isolated but most...Ch. 17.13 - Prob. 43PCh. 17.13 - Prob. 44PCh. 17.13 - What products would be formed from the proceedings...Ch. 17.13 - a. In a six-step synthesis, what is the yield of...Ch. 17.13 - Show how each of the following compounds could be...Ch. 17.15 - Prob. 48PCh. 17.17 - Prob. 50PCh. 17.18 - Prob. 51PCh. 17.19 - Prob. 52PCh. 17 - Draw the structure for each of the following: a....Ch. 17 - Prob. 54PCh. 17 - Prob. 55PCh. 17 - a. Show the reagents required to form the primary...Ch. 17 - Prob. 57PCh. 17 - Using cyclohexanone as the starting material,...Ch. 17 - Prob. 59PCh. 17 - 60. Show how each of the following compounds could...Ch. 17 - Fill in the boxes:Ch. 17 - Prob. 62PCh. 17 - Identify A through O:Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Prob. 66PCh. 17 - How many signals would the product of the...Ch. 17 - Prob. 68PCh. 17 - Prob. 69PCh. 17 - Prob. 70PCh. 17 - Prob. 71PCh. 17 - Prob. 72PCh. 17 - Prob. 73PCh. 17 - Prob. 74PCh. 17 - Prob. 75PCh. 17 - Prob. 76PCh. 17 - Prob. 77PCh. 17 - A compound gives the following IR spectrum. Upon...Ch. 17 - a. Propose a mechanism for the following reaction:...Ch. 17 - Prob. 80PCh. 17 - Prob. 81PCh. 17 - Prob. 82PCh. 17 - Prob. 83PCh. 17 - Prob. 84PCh. 17 - In the presence of an acid catalyst, acetaldehyde...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - A compound reacts with methylmagnesium bromide...Ch. 17 - Show how each of the following compounds can be...Ch. 17 - Prob. 91PCh. 17 - Prob. 92PCh. 17 - The pKa values of the carboxylic acid groups of...Ch. 17 - The Baylis-Hillman reaction is a DABCO...Ch. 17 - Prob. 95PCh. 17 - Prob. 96P
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- Construct flow charts (a.k.a. flow diagrams) to show how to separate each of the following pairs ofwater insoluble compounds:a) a carboxylic acid and a neutral compound (e.g., a hydrocarbon, R-H);b) a neutral compound and an amine;c) a phenol, a carboxylic acid and an amine.arrow_forwardWhy would the following reaction first produce an amide and then convert it back to the starting meterialarrow_forwardGiven the information pictured, The final step of the reaction sequence uses PhLi. Provide a reason and possible mechanism by which this final elimination and hydrolysis reaction would occur.arrow_forward
- Amidation Reactions Part A Learning Goal: To identify characteristics common to all amidation reactions, and to apply these generalities in drawing specific amidation reactants or products. Part B Amidation reactions are condensation reactions. In a condensation reaction, two molecules join with a new covalent bond, and this results from the removal of a small molecule such as a water molecule. The reactants in amidation are a carboxylic acid and an amine, and the products are an amide and a water molecule. The carboxylic acid reactant can be of any type. The amine can be simple ammonia (NH₂). a primary amine. or a secondary amine. It cannot be a tertiary amine because tertiary amines lack the N-H Aspartame, an amide, is the sweetener commonly used in diet cola. COOH CH2 < 33 of 38 Review | Constants | Periodic Table CH2 O H₂N CH C NH-CH-COOCH3 7 H 2D EXP. CONT. aspartame Draw the carboxylic acid that is a reactant in the production of aspartame. Draw the molecule on the canvas by…arrow_forwardWrite the step by step mechanism with curved arrows of the hydrolysis of the amide in this reaction.arrow_forwardPrimary amines can also be prepared by the reaction of an alkyl halide with azide ion, followed by catalytic hydrogenation. What advantage do this method and the Gabriel synthesis have over the synthesis of a primaryamine using an alkyl halide and ammonia?arrow_forward
- Draw a flow-chart for the separation of benzoic acid and ethyl benzoate . Which compound can be found in which step, in which form and where?arrow_forwardVanillic acid is the oxidized phenolic derivative of vanillin. By using Proton Nuclear Magnetic Resonance ('H-NMR) spectroscopic technique, point out the difference that can be observed between vanillin and vanillic acid in terms of chemical shift based on its chemical structures. но Он Vanillic acid Vanillinarrow_forwardPrimary amines can also be prepared by the reaction of an alkyl halide with azide ion, followed by catalytic hydrogenation. What advantage do this method and the Gabriel synthesis have over the synthesis of a primary amine using an alkyl halide and ammonia?arrow_forward
- 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_forwardComplete the following proposed acid–base reactions, and predict whether the reactants or products are favored.arrow_forwardAnswer the following questions based on the information provided. (a) Sildenafil (Viagra) is used to treat erectile dysfunction (impotence; inability to get or keep an erection) in men. Sildenafil (Revatio) is used to improve the ability to exercise in adults with pulmonary arterial hypertension. One of the key step of Sildenafil synthesis is shown below. OEt O OEt O i) Amine HO CHO ii) H20 washing to remove the HCI residue CI N. i) What's the structure of Amine reagent? Amine structure ii) Why does not carboxyl acid react with amine? iii) Draw the mechanism of the reaction.arrow_forward
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