Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Textbook Question
Chapter 15.1, Problem 15.2P
Recalling the reactions of alcohols from Chapter 10, show how to synthesize each compound from an organohalogen compound and an oxirane, followed by a transformation of the resulting hydroxyl group to the desired oxygen-containing
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Prepare the following compounds starting from benzaldehyde and the appropriate ketone. Provide reactions for preparing the ketones starting from aromatic hydrocarbon compounds.
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Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures,
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3-methyl-2-butanol
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Major Product
Minor Product
Minor Product
Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second
molecule of alcohol gives an acetal and a molecule of water.
ROH, H+
OH
OR
Aldehyde/ketone
Alcohol
ROH, H+
Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds:
OH
OH
OR
OR
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
+ H₂O
Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Explain how these Grignard reagents would react...Ch. 15.1 - Recalling the reactions of alcohols from Chapter...Ch. 15.2 - Prob. 15.3PCh. 15.2 - Show how to prepare each Gilman reagent in Example...Ch. 15.2 - Predict the product of the following reaction.Ch. 15.2 - Show how the following compound could be prepared...Ch. 15 - Complete these reactions involving lithium...Ch. 15 - Show how to convert 1-bromopentane to each of...Ch. 15 - Prob. 15.9PCh. 15 - Show how to prepare each compound from the given...
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Show how the following compound can be prepared in...Ch. 15 - Prob. 15.15PCh. 15 - Show how spiro[2.2]pentane can be prepared in one...Ch. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - We now continue the introduction of organic...Ch. 15 - Write the products of the following sequences of...Ch. 15 - Using your old and new reaction roadmaps as a...Ch. 15 - Using your old and new reaction roadmaps as a...Ch. 15 - Using your old and new reaction roadmaps as a...Ch. 15 - Using your old and new reaction roadmaps as a...Ch. 15 - Prob. 15.25PCh. 15 - Gilman reagents are versatile reagents for making...
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- Hydration of aldehydes and ketones can be catalyzed by acid or base. Bases catalyze hydration by: protonating the carbonyl oxygen making the carbonyl group more electrophilic employing hydroxide ion, which is a better nucleophile than water making the carbonyl group less electrophilic shifting the equilibrium position of the reaction to favor productsarrow_forwardGive the reagents and intermediate products for the following two-step reaction.arrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forward
- Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)arrow_forwardA synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.arrow_forwardb) The Wolf-Kishner reduction is a reaction used in Organic Chemistry to convert carbonyl functionalities into methylene group. The reaction was used to convert an aldehyde or ketone to an alkane using hydrazine, base and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone. Stage 1: The reaction of aldehyde/ketone with hydrazine to produce hydrazine Stage 2: Reaction with the base and heat to convert hydrozone to alkane Write the mechanism of the reaction.arrow_forward
- Following is the structural formula of the tranquilizer meparfynol (Oblivon). Oblivon HO Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains al- kyne and hydroxyl functional groups.)arrow_forwardGive the systematic (IUPAC) names for these molecules. Boononon cnolonongron. НаСНз CHОССH2СH2СНCHЗ CH3 phenyl propanoate |4-methyl pentane methanoat Incorrect. You mixed up the acyl and alkoxy portions of the molecule. Name the alkoxy part first, followed by the acyl part.arrow_forward4-pyranone will readily undergo an acid-base reaction. Identify the reaction conditions that will result in the formation of an aromatic product. Then, draw the aromatic resonance product structure. Include all lone pairs in your structure. Ignore inorganic byproducts. H3O+arrow_forward
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