Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 17.13, Problem 43P
(a)
Interpretation Introduction
Interpretation:
The product has to be predicted for the proceeding reaction with
(b)
Interpretation Introduction
Interpretation:
The reagent could be used to reduce only the keto group has to be predicted.
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The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols.
a. Why does the Ritter reaction not work with primary alcohols?
b. Provide an explanation for why an amide is less susceptible to nucleophilic attack than its corresponding ester.
The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols.
a. Propose a mechanism for the Ritter reaction.b. Why does the Ritter reaction not work with primary alcohols?c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?
a. Would you expect hemiacetals to be stable in basic solutions? Explain your answer.b. Acetal formation must be catalyzed by an acid. Explain why it cannot be catalyzed by CH3O-.c. Can the rate of hydrate formation be increased by hydroxide ion as well as by acid? Explain.
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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- The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols. a. Propose a mechanism for the Ritter reaction. b. Why does the Ritter reaction not work with primary alcohols? c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?arrow_forwardThiols or thiol (-SH) group is a better base than hydroxide (-OH) group in elimination reactions.arrow_forwardWhat is the purpose of the first step of this reaction? OH 1. CH;CH,OH, H* 2. LIAIH4, Et,0 3. H*, H,0 Create an enolate on the a-carbon Reduce the ester Protect that aldehyde as an acetal Hydrolyze the ester to promote reactivity of the carboxylic acid derivativearrow_forward
- What reagents would you use to convert methyl propanoate to the following compounds? a. isopropyl propanoate b. sodium propanoate c. N-ethylpropanamide d. propanoic acidarrow_forwardWhat is the role of triethylamine in this reaction? Draw the curly arrow reaction mechanism to show bonds being broken/formed.arrow_forwardd. Provide an arrow-pushing mechanism for the reaction. OH 1. NaOH 2. CH3CH₂ so acetaminophen phenacetinarrow_forward
- Which of the following statements is INCORRECT? a. The electronegative oxygen atom of the α,β-unsaturated carbonyl compound withdraws electrons from the β-carbon leading to more electron-poor characteristic for the carbon than a typical alkene C=C bond. b. A carbon–oxygen double bond is structurally similar to a carbon–carbon double bond. c. Aldehyde and ketones usually react irreversibly with alcohols or water to yield acetals or vicinal diol respectively. d. The carbonyl carbon atom is sp2-hybridized and forms both sp2 σ-bond and a p π-bond to oxygen.arrow_forwardWhat is the reaction mechanism for formaldehyde and phenol under acidic conditions?arrow_forwardPhosgene (COCl2) was used as a poison gas in World War I. What product would be formed from the reaction of phosgene with each of the following reagents? a. one equivalent of methanol b. excess methanol c. excess propylamine d. excess waterarrow_forward
- From which starting materials can the product formed as a result of the following reaction be synthesized? A. Acetophenone and butanal B. Benzaldehyde and 3-pentanone C. Benzaldehyde and 2-pentanone D. Acetophenone and 2-butanonearrow_forward1. The alkene mixture obtained on dehydration of 2,2-dimethylcyclohexanol contains a significant amount of 1,2-dimethylcyclohexene a. Draw the structure of 1,2-dimethylcyclohexene b. Show a mechanism for the formation of this alkene product c. Draw the structures and give the names of any other alkene products, explaining how they could arise from the dehydration reactionarrow_forward10. Why do aldehydes undergo nucleophilic addition reactions (rxns from Unit 10) while esters undergo nucleophilic acyl substitution (rxns from Unit 11) reactions? A) The carbonyl carbon of an ester is more electrophilic than that of an aldehyde. B) Aldehydes are more sterically hindered than esters. C) Once the nucleophile adds to an aldehyde, the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups. D) The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized. E) Once the nucleophile adds to an aldehyde, neither H- nor R- can be eliminated since they are strongly basic.arrow_forward
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