Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 7.13, Problem 20P
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we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?
Treatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.
Propose a synthesis for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any reagents and solvents.
Trans-cyclopentane-1,2-diol.
Chapter 7 Solutions
Organic Chemistry - Standalone book
Ch. 7.1 - Name each of the following using IUPAC...Ch. 7.1 - Prob. 2PCh. 7.2 - How many carbon atoms are sp2-hybridized in the...Ch. 7.3 - Prob. 4PCh. 7.3 - Are cis-2-hexene and trans-3-hexene stereoisomers?...Ch. 7.4 - Prob. 6PCh. 7.4 - Prob. 7PCh. 7.4 - Give the IUPAC name of each of the compounds in...Ch. 7.5 - Arrange the following in order of increasing...Ch. 7.6 - Prob. 10P
Ch. 7.6 - Standard enthalpies of formation are known for all...Ch. 7.6 - Prob. 12PCh. 7.6 - Despite numerous attempts, the alkene...Ch. 7.6 - Write structural formulas for the six isomeric...Ch. 7.7 - Place a double bond in the carbon skeleton shown...Ch. 7.9 - Identify the alkene obtained on dehydration of...Ch. 7.10 - Prob. 17PCh. 7.11 - Prob. 18PCh. 7.12 - Prob. 19PCh. 7.13 - The alkene mixture obtained on dehydration of...Ch. 7.14 - Write the structures of all the alkenes that can...Ch. 7.14 - Write structural formulas for all the alkenes that...Ch. 7.15 - A study of the hydrolysis behavior of...Ch. 7.15 - Use curved arrows to illustrate the electron flow...Ch. 7.15 - Predict the major product of the reaction shown.Ch. 7.16 - Prob. 26PCh. 7.17 - Prob. 27PCh. 7.18 - Prob. 28PCh. 7.19 - Predict the major organic product of each of the...Ch. 7.19 - A standard method for the synthesis of ethers is...Ch. 7 - Write structural formulas for each of the...Ch. 7 - Prob. 32PCh. 7 - Give an IUPAC name for each of the following...Ch. 7 - A hydrocarbon isolated from fish oil and from...Ch. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Choose the more stable alkene in each of the...Ch. 7 - Suggest an explanation for the fact that...Ch. 7 - Prob. 41PCh. 7 - Write structural formulas for all the alkene...Ch. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Predict the major organic product of each of the...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - The rate of the reaction In the first order in...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - You have available 2,2-dimethylcyclopentanol (A)...Ch. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Acid-catalyzed dehydration of...Ch. 7 - The ratio of elimination to substitution is...Ch. 7 - Prob. 57PCh. 7 - Prob. 58DSPCh. 7 - Prob. 59DSPCh. 7 - Prob. 60DSPCh. 7 - Prob. 61DSPCh. 7 - A Mechanistic Preview of Addition Reactions The...Ch. 7 - Prob. 63DSPCh. 7 - Prob. 64DSPCh. 7 - Prob. 65DSP
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- What major alkene product is expected for the dehydration of 2-methylcyclohexanol? What key differences in the infrared spectrum would you expect when comparing the starting material (2-methylcyclohexanol) to the major alkene product?arrow_forward-Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.arrow_forwardWittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forward
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