EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
6th Edition
ISBN: 9781305687875
Author: Gilbert
Publisher: CENGAGE LEARNING - CONSIGNMENT
expand_more
expand_more
format_list_bulleted
Question
Chapter 10.3, Problem 7E
Interpretation Introduction
Interpretation:To explain the cause that the given tactic is not a good option for the dehydration of 4-methyl-2-pentanol and cyclohexanol.
Concept introduction:Dehydration reaction is a conversion that involves the loss of water from the reacting molecule or ion. Dehydration reactions are the reverse of hydration reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Can you please fill the rest of this chart
A chemist desires to dehydrate 1-octanol.
What is the expected product, and would a higher or lower temperature be needed for the first distillation?
Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.
Chapter 10 Solutions
EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
Ch. 10.2 - Prob. 1ECh. 10.2 - Prob. 2ECh. 10.2 - Prob. 3ECh. 10.2 - Prob. 4ECh. 10.2 - Prob. 5ECh. 10.2 - Prob. 6ECh. 10.2 - Prob. 7ECh. 10.2 - Prob. 8ECh. 10.2 - Prob. 9ECh. 10.2 - Prob. 10E
Ch. 10.2 - Prob. 11ECh. 10.2 - Prob. 12ECh. 10.2 - Prob. 13ECh. 10.2 - Prob. 14ECh. 10.2 - Prob. 15ECh. 10.2 - Prob. 16ECh. 10.2 - Prob. 17ECh. 10.3 - Prob. 1ECh. 10.3 - Prob. 2ECh. 10.3 - Prob. 3ECh. 10.3 - Prob. 4ECh. 10.3 - Prob. 5ECh. 10.3 - Prob. 6ECh. 10.3 - Prob. 7ECh. 10.3 - Prob. 8ECh. 10.3 - Prob. 9ECh. 10.3 - Prob. 10ECh. 10.3 - Prob. 11ECh. 10.3 - Prob. 12ECh. 10.3 - Prob. 13ECh. 10.3 - Prob. 14ECh. 10.3 - Prob. 15ECh. 10.3 - Prob. 16ECh. 10.3 - Prob. 17ECh. 10.3 - Prob. 18ECh. 10.3 - Prob. 19ECh. 10.3 - Prob. 20ECh. 10.3 - Prob. 21ECh. 10.3 - Prob. 22ECh. 10.3 - Prob. 23ECh. 10.3 - Prob. 24ECh. 10.3 - Prob. 25ECh. 10.3 - Prob. 26ECh. 10.3 - Prob. 27ECh. 10.3 - Prob. 28ECh. 10.3 - Prob. 29ECh. 10.3 - Prob. 30ECh. 10.3 - Prob. 31ECh. 10.3 - Prob. 32ECh. 10.5 - Prob. 1ECh. 10.5 - Prob. 2ECh. 10.5 - Prob. 3ECh. 10.5 - Prob. 4ECh. 10.5 - Prob. 5ECh. 10.5 - Prob. 6ECh. 10.5 - Prob. 7ECh. 10.5 - Prob. 8ECh. 10.5 - Prob. 9ECh. 10.5 - Prob. 10ECh. 10.5 - Prob. 11ECh. 10.5 - Prob. 12ECh. 10.5 - Prob. 14ECh. 10.5 - Prob. 15ECh. 10.5 - Prob. 16ECh. 10.5 - Prob. 17ECh. 10.5 - Prob. 18ECh. 10.5 - Prob. 19ECh. 10.5 - Prob. 20ECh. 10.5 - Prob. 23ECh. 10.6 - Prob. 1ECh. 10.6 - Prob. 2ECh. 10.6 - Prob. 3ECh. 10.6 - Prob. 4ECh. 10.6 - Prob. 5ECh. 10.6 - Prob. 6ECh. 10.6 - Prob. 7ECh. 10.6 - Prob. 8ECh. 10.6 - Prob. 9ECh. 10.6 - Prob. 10ECh. 10.6 - Prob. 11ECh. 10.6 - Prob. 12ECh. 10.6 - Prob. 13ECh. 10.6 - Prob. 14ECh. 10.6 - Prob. 15ECh. 10.6 - Prob. 16ECh. 10.6 - Prob. 17ECh. 10.6 - Prob. 18ECh. 10.6 - Prob. 20ECh. 10.6 - Prob. 21ECh. 10.6 - Prob. 22ECh. 10.6 - Prob. 23ECh. 10.6 - Prob. 24ECh. 10.6 - Prob. 25ECh. 10.6 - Prob. 26ECh. 10.6 - Prob. 28ECh. 10.6 - Prob. 29ECh. 10.6 - Prob. 30ECh. 10.7 - Prob. 1ECh. 10.7 - Prob. 2ECh. 10.7 - Prob. 3ECh. 10.7 - Prob. 4ECh. 10.7 - Prob. 5ECh. 10.7 - Prob. 6ECh. 10.7 - Prob. 7ECh. 10.7 - Prob. 8ECh. 10.7 - Prob. 9ECh. 10.7 - Prob. 10ECh. 10.7 - Prob. 11ECh. 10.7 - Prob. 12ECh. 10.8 - Prob. 1ECh. 10.8 - Prob. 2ECh. 10.8 - Prob. 4ECh. 10.8 - Prob. 5ECh. 10.8 - Prob. 6ECh. 10.8 - Prob. 7ECh. 10.8 - Prob. 8ECh. 10.8 - Prob. 9ECh. 10.8 - Prob. 10ECh. 10.8 - Prob. 11ECh. 10.8 - Prob. 12ECh. 10.8 - Prob. 13ECh. 10.8 - Prob. 14ECh. 10.8 - Prob. 15E
Knowledge Booster
Similar questions
- Write the esterification reaction of acetic acid with isopentyl alcohol to form isopentyl acetate and acetic acid. What is the theortical yield of isopentyl acetate and which one is the liniting reagent? Moles of acetic anhydride= 0.023mol Volume of acetic anhydride= 2.2ml Molar mass of acetic anhydride= 102.09g/mol Volume of isopentyl acetate = 2ml Molar mass of isopentyl acetate = 88.148g/mol Density of isopentyl acetate = 0.81g/mL Mass of isopentyl acetate (Actual yield)= 1.887garrow_forwardIsopropanol is a good extraction solvent for plant pigments as it breaks down cell walls and is miscible with pigments. Can you be sure that you only extracted chlorophyll-a from your spinach leaf? If not, what else might have been extracted?arrow_forwardDescribe the process (Step by Step) of the fractional distillation of 4-t-butylcyclohexanol and 4-t-butylcyclohexenearrow_forward
- You are asked by your chemistry teacher to find: a) the solubility of different carboxylic acids in water and b) whether there is a connection between solubility and structure of different carboxylic acids. Follow the questions below to design and conduct an experiment to determine an answer to this question. a. From the paragraph above, write a question out that you will try and answer from conducting an experiment (C:2) b. Based upon your knowledge of the physical properties of organic compounds, hypothesize an order of solubility from lowest to highest: (1:3) Organic Compound Order of solubility (1=lowest, 3=highest) Pentanoic acid Hexanoic acid Ethanoic acid c. Provide an overall explanation for your hypothesis based upon your knowledge of physical properties. (A:3) d. Based upon the materials listed below, design a step by step experiment to test your hypothesis. Provide your individual steps. Include all the materials listed below. (1:3) Materials: CH,(CH,4COOH (), CH,COOH (),…arrow_forwardWhy does the dehydration of an alcohol more often use concentrated sulfuric acid, H2SO4H2SO4, as the acid catalyst rather than dilute hydrochloric acid, HCl? Select one or more: Hydrochloric acid is too small to effectively react with the alcohol in the reaction. The additional water solvent from a dilute solution could reverse the dehydration reaction. Only acids with more than one proton can complete the dehydration reaction. The presence of the chloride ion could result in a competing substitution reaction.arrow_forwardWhat type of chemical intermediate plays an important role in causing primary, secondary, and tertiary alcohols to react at different rates in the Lucas test? Explain how this chemical intermediate controls the rates of reaction of the different alcohols.arrow_forward
- Question 4. phthalate and dibutyl phthalate in an inert solvent like chloroform. Both steps of this reaction rapidly establish equilibrium. In this system, would you expect adding an equimolar amount of one reagent dropwise to the other to affect the outcome of the reaction? Explain your response. Consider the acid-catalyzed esterification of phthalic acid to form buthyl (K =~1.0) H* .COOH H20 но CHCI3 СООН СООН phthalic acid butanol butyl phthalate (K=~1.0) H* но + H20 CHCI3 `COOH butyl phthalate butanol dibutyl phthalate O=U O=0 0=Carrow_forwardFor these two equilibrium systems, production of ethanol for ethene esterification Make a detailed description of the technology including the following: efficiency of process source(s) of the reactants Thank you! Dont use cursive please.arrow_forwardWhich of the following statements is not correct? Oxymercuration-demercuration for alcohol synthesis is complicated by carbocation rearrangement. Oxymercuration-demercuration for alcohol synthesis follows Markonikov's Rule. Sodium borohydride is used in the last step of oxymercuration-demercuration to oxidize the hydroxyalkyl mercury compound. All of the above. Both the 1st and the 3rd statements.arrow_forward
- Methyl benzoate can be synthesized by a Fisher Esterification reaction, and then this ester can be used as a starting material in the grignard synthesis of triphenyl carbinol. Suppose that in the synthesis of methyl benzoate, a student started with 12 grams of benzoic acid and 29.86 ml of methanol. After finishing the preparation of the ester, 7.63 grams of methylbenzoate was obtained, and the benzoic acid reacted completely. What is the percent yield of the ester? ( density methanol = 0.791 g/ml, methanol = 32.04 g/mol, methyl benzoate = 136.15 g/mol, benzoic acid = 122.12 g/mol )arrow_forwardHow could you separate a mixture of ethanol, 1-pentanol and 1-octanol. Discuss the steps in your procedure.arrow_forwardThe flavors and aromas of almost any fruit are primarily due to esters. In an experiment, an artificial fruit flavor is prepared using the Fischer esterification (reaction of an alcohol with a carboxylic acid in the presence of sulfuric acid catalyst). Why is sodium bicarbonate solution used in the workup of the reaction? What advantage does sodium bicarbonate have over sodium hydroxide solution?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
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chemistry: Matter and Change
Chemistry
ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Publisher:Glencoe/McGraw-Hill School Pub Co