Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 10, Problem 93P
(a)
Interpretation Introduction
Interpretation:
The product should be identified.
Concept introduction:
The pinacol–pinacolone rearrangement:
Pinacol–pinacolone rearrangement is a conversion of 1,2-
(b)
Interpretation Introduction
Interpretation:
The reason should be explained for the only one product in the given reaction.
Concept introduction:
The pinacol–pinacolone rearrangement:
Pinacol–pinacolone rearrangement is a conversion of 1,2-diol to a carbonyl compound in the presence of acid via 1,2- shift is called rearrangement is called Pinacol–pinacolone rearrangement.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
5. WHAT IS GRIGNARD REACTION? WHAT CONSTITUTES A GRIGNARD REAGENT?
6. WHAT IS KETO-ENOL TAUTOMERIZATION?
Heating an alcohol with sulfuric acid is a good way to prepare a symmetrical ether such as diethyl ether.
a. Explain why it is not a good way to prepare an unsymmetrical ether such as ethyl propyl ether.
b. How would you synthesize ethyl propyl ether?
Fischer Esterification
2.) Why is sodium bicarbonate solution used in the work up of the reaction? What advantage does sodium bicarbonate have over sodium hydroxide solution?
3.) Why is it easier to remove excess carboxylic acid from the product than excess alcohol?
Chapter 10 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 10.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 10.1 - Explain the difference in reactivity between...Ch. 10.1 - Prob. 5PCh. 10.1 - Prob. 6PCh. 10.1 - Prob. 8PCh. 10.2 - Prob. 9PCh. 10.3 - Prob. 11PCh. 10.3 - Show how 1-propanol can be converted into the...Ch. 10.4 - Which of the following alcohols dehydrates the...Ch. 10.4 - Prob. 14P
Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
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
- The PKa of p-nitrophenol is 7.15. Would you expect this to dissolve in a sodium bicarbonate solution? The PKa of 2,5-dinitrophenol is 5.15. Will it dissolve in bicarbonate solution?arrow_forwardWhy is it not advisable to use aqueous hydrochloric acid in a Grignard reaction of a ketone? A) The Grignard reagent will react with the acid and cannot react with the ketone. B) The ketone will be protonated and will become unreactive. C) The ketone will form an unreactive enol. D) The Grignard reagent won't dissolve in aqueous solutionsarrow_forward2. Sodium Borohydride Reduction of Vanillin a. What is the purpose of adding HCl at the end of reaction? b. How will the vanillyl alcohol be idenarrow_forward
- 1. Which compound is expected to have a higher melting point, 1-pentanol or 1-pentanal? Explain 2. Which compound is expected to be more soluble in water, propanal or butanal? Explain. 3. Why is acetyl chloride more reactive towards hydrolysis than ethyl acetate?arrow_forwardExplain why the ortho-substituted 2-nitrophenol in 30-40% yield and the para-substituted 4-nitrophenol in 15% yield have different boiling points and in doing so, explain which isomer has the higher boiling point and which one has the lower boiling point?arrow_forwardExplain the mechanism of Oxidation of an Alcohol with CrO3 ?arrow_forward
- 1. Explain the solubility behavior of the alcohols and phenols in water as a function of: a. Branching in the structure b. Relative proportion of hydrophilic to hydrophobic bonds 2. Based on oxidation test, classify the alcohols and phenols according to the following categories: easily oxidizable, oxidizable, and resistant to oxidation. 3. Explain in 2 – 3 sentences the reactivity differences of the alcohols towards the Lucas reagent. 4. Explain in 2 – 3 sentences the solubility of alcohols and phenols in water.arrow_forwardWhen performing a Grignard reaction it is also very important that the reaction be free from acetone (a chemical we commonly use to clean the glassware). Why must the glassware be free from acetone? A. Acetone reacts with the diethyl ether causing a side reaction to occur B. Acetone is a nucleophile that will react with the Grignard reagent C. Acetone reacts with the bromobenzene D. Acetone is an electrophile that will react with the Grignard reagentarrow_forwardThe 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.arrow_forward
- What product is formed when CH3OCH2CH2C ≡ CCH2CH(CH3)2 is treated with each reagent: (a) H2 (excess), Pd-C; (b) H2(1 equiv), Lindlar catalyst; (c) H2 (excess), Lindlar catalyst; (d) Na, NH3?arrow_forwardWhen synthesizing acetals and ketals, what is the main driving force behind whether the reaction favors the carbonyl species or the acetal/ketal? a the catalytic acid b solvent c temperature d Le Châtelier's Principlearrow_forwardDraw the major organic product for the reaction between 1,2-dimethylcycloheptene and a cold, dilute solution of KMnO4.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole