Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 9, Problem 37P
The oxidation step involves an enol intermediate. Using Mechanism
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
single reaction sequence: a certain ketone undergoes alkylation to give new ketone, when reacted with a base and then an alkylating agent, 1-bromopropane. What is the structure of the final ketone product?
1) Nucleophilic substitution reaction of alkyl halide is a process when nucleophile replace
the leaving group of alkyl halide. Propose the mechanism and product(s) for the
following substitution reaction.
b) 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.
Chapter 9 Solutions
Organic Chemistry - Standalone book
Ch. 9.1 - Prob. 1PCh. 9.2 - Prob. 2PCh. 9.4 - How do bond distances and bond strengths change...Ch. 9.5 - Complete each of the following equations to show...Ch. 9.6 - Prob. 5PCh. 9.6 - Which of the alkynes of molecular formula C5H8 can...Ch. 9.7 - Give the structures of three isomeric dibromides...Ch. 9.7 - Prob. 8PCh. 9.9 - Write a series of equations showing how you could...Ch. 9.9 - Write a series of equations showing how to prepare...
Ch. 9.10 - Prob. 11PCh. 9.11 - Give the structure of the enol formed by hydration...Ch. 9.11 - Prob. 13PCh. 9.13 - Prob. 14PCh. 9.14 - Prob. 15PCh. 9 - Provide the IUPAC name for each of the following...Ch. 9 - Prob. 17PCh. 9 - All compounds in Problem 9.17 are isomers except...Ch. 9 - Prob. 19PCh. 9 - Write structural formulas for all the alkynes of...Ch. 9 - Prob. 21PCh. 9 - Prob. 22PCh. 9 - The alkane formed by hydrogenation of...Ch. 9 - Write the structure of the major organic product...Ch. 9 - Write the structure of the major organic product...Ch. 9 - When 2-heptyne was treated with aqueous sulfuric...Ch. 9 - Prob. 27PCh. 9 - Prob. 28PCh. 9 - Prob. 29PCh. 9 - Show by writing appropriate chemical equations how...Ch. 9 - Show by writing appropriate chemical equations how...Ch. 9 - Diphenylacetylene can be synthesized by the double...Ch. 9 - (Z)-9-tricosene [ (Z)-CH3(CH2)7CH=CH(CH2)12CH3 ]...Ch. 9 - Prob. 34PCh. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Alkynes undergo hydroboration to give...Ch. 9 - Prob. 38DSPCh. 9 - Prob. 39DSPCh. 9 - Prob. 40DSPCh. 9 - Prob. 41DSPCh. 9 - Thinking Mechanistically About Alkynes The...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.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_forward1.Treatment of 3-methyl-2-butanol with hydrogen chloride yielded only a trace amount of 2-chloro-3-methylbutane. An isomeric chloride was isolated in 97% yield. Explain why an isomeric compound is formed instead, andsuggest a reasonable structure for this product. 2) Acid-catalyzed hydration of 2-Methyl-1-butene yields two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explain why, by showing the structures of the products. 3) The Williamson ether synthesis cannot be used to prepare tert-butyl phenyl ether. Explain why this method cannot be used in this case. 4) Show the structure of the main product when 2,2-dimethyloxirane reacts in methanol. (a) in the presence of an acid, (b) with added sodium methoxide.arrow_forward
- Write the expected substitution product(s) for each reaction and predict the mechanism by which each product is formedarrow_forwardDraw structural formulas for the isomeric carbocation intermediates formed on treatment of each alkene with HCl. Label each carbocation 1°, 2°, or 3° and state which of the isomeric carbocations forms more readily.arrow_forwardWrite a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.arrow_forward
- Alkylation of benzene with 1-chlorobutane in the presence of AlCl3 gave not only the expected butylbenzene product but also, as a major product, (1-methylpropyl)benzene. Write an equation for the reaction Propose a mechanism to account for the formation of butylbenzene Propose a mechanism to account for the formation of (1-methylpropyl)benzenearrow_forwardChoose the correct product and Furnish a step-by-step electron-flow diagram that elucidates the transformation of the product from the enol generated in the second step (that is, illustrate the mechanism by which the enol is converted into a ketone). Explain in detailsarrow_forwardH3C N- H₂NNH₂ H⭑ CH3 H3C IN CH3 Hydrazine reacts with 2,4-pentanedione to yield 3,5-dimethylpyrazole. Including protonations and deprotonations, the reaction takes 12 steps. Write out the mechanism on a sheet of paper and then draw the structure of the product of step 6. • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • In an elimination step, include the structure of the leaving group, but draw it in its own sketcher. Separate structures with + signs from the drop-down menu. ? Sn th Previous Nextarrow_forward
- When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (1). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (2) and the bicyclic ether (3). (a) Propose a mechanism for formation of product (1), and account for its configuration. (b) Propose a mechanism for formation of product (2). (c) Account for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardEthylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License