Organic Chemistry (Looseleaf) - With Access
7th Edition
ISBN: 9780134325774
Author: Bruice
Publisher: PEARSON
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Chapter 17, Problem 91P
Interpretation Introduction
Interpretation:
The reaction mechanism for the given ring expansion reaction has to be given.
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When a cyclic ketone reacts with diazomethane, the next larger cyclic ketone is formed. This is called a ring-expansion reaction. Draw a mechanism for the following ring-expansion reaction.
When a cyclic ketone reacts with diazomethane, the next larger cyclic ketone is formed. This is called a ring-expansion reaction. Draw a mechanism forthe following ring-expansion reaction.
propose a mechanism for the following transformations
Chapter 17 Solutions
Organic Chemistry (Looseleaf) - With Access
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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- A Cannizzaro reaction is the reaction of an aldehyde that has no a-hydrogens with concentrated aqueous sodium hydroxide. In this reaction, half the aldehyde is converted to a carboxylic acid and the other half is converted to an alcohol. Propose a mechanism for the following Cannizzaro reaction:arrow_forwardA Cannizzaro reaction is the reaction of an aldehyde that has no a-hydrogens with concentrated aqueous sodium hydroxide. In this reaction, half thealdehyde is converted to a carboxylic acid and the other half is converted to an alcohol. Propose a mechanism for the following Cannizzaro reaction:arrow_forwardPropose a possible reaction mechanism for the following transformation. Draw out the steps with the correct reaction arrows.arrow_forward
- Propose a mechanism for the following transformationarrow_forwardThe Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde to form an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)arrow_forwardA vicinal diol has OH groups on adjacent carbons. The dehydration of a vicinal diol is accompanied by a rearrangement called the pinacol rearrangement. Propose a mechanism for this reaction.arrow_forward
- Propose a mechanism for the followingreaction → NaOH,acetonearrow_forwardWhen propionaldehyde is warmed with sodium hydroxide, one of the products is2-methylpent-2-enal. Propose a mechanism for this reaction.arrow_forwardTreatment of cis-2-bromocyclohexanol with NaOH yields cyclohexanone instead of an epoxide. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism.arrow_forward
- Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction. For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. Propose a mechanism.arrow_forwardClaisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.arrow_forwardThe Favorskii reaction involves treatment of an -bromo ketone with base to yield a ring-contracted product. For example, reaction of 2-bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid. Propose a mechanism.arrow_forward
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