ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582422
Author: Brown
Publisher: CENGAGE L
expand_more
expand_more
format_list_bulleted
Question
Chapter 10, Problem 10.57P
Interpretation Introduction
Interpretation:
Synthetic intermediates A and B have to be drawn.
Concept Introduction:
Conversion of alcohol into
Conversion of primary and secondary alcohols to Chloroalkane is thionyl chloride. The reaction is carried out in the presence of base such as pyridine or trimethylamine.
The reaction of an alcohol with thionyl chloride is the formation of an alkyl Chlorosulfite that converts hydroxide ion (poor leaving group) into Chlorosulfite (good leaving group). Nucleophilic displacement of this leaving group gives product.
Leaving group: Leaving group can be any groups or atoms that get detached from either neutral or charged organic compounds. The stability of the leaving group is to stabilize the electron density that results from heterolysis cleavage of bond.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Explain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.
The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents.
1-Octen-3-ol is a potent mosquito attractant commonly used in mosquito traps. A number of reactions, including hydrogenation, will transform 1-octen-3-ol into a less effective molecule. Draw the structure of a hydrogenation product of 1-octen-3-ol.
Chapter 10 Solutions
ORGANIC CHEMISTRY-OWL V2 ACCESS
Ch. 10.1 - Write IUPAC names for these alcohols and include...Ch. 10.1 - Classify each alcohol as primary, secondary, or...Ch. 10.1 - Write IUPAC names for these unsaturated alcohols.Ch. 10.2 - Arrange these compounds in order of increasing...Ch. 10.2 - Prob. 10.5PCh. 10.4 - Predict the position of equilibrium for this...Ch. 10.5 - Show how to convert (R)-2-pentanol to...Ch. 10.6 - Draw structural formulas for the alkenes formed by...Ch. 10.6 - Propose a mechanism to account for this...Ch. 10.7 - Propose a mechanism to account for the following...
Ch. 10.7 - Prob. AQCh. 10.7 - Prob. BQCh. 10.7 - Prob. CQCh. 10.7 - Prob. DQCh. 10.7 - Which step in the reaction would you expect to be...Ch. 10.7 - Prob. FQCh. 10.7 - Prob. GQCh. 10.8 - Prob. 10.11PCh. 10.8 - Prob. AQCh. 10.8 - Prob. BQCh. 10.8 - Prob. CQCh. 10.8 - Why does nature use a reagent as complex as NAD+...Ch. 10.8 - -Hydroxyketones and -hydroxyaldehydes are also...Ch. 10.9 - Write IUPAC names for these thiols.Ch. 10 - Which are secondary alcohols?Ch. 10 - Name each compound.Ch. 10 - Prob. 10.16PCh. 10 - Name and draw structural formulas for the eight...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Arrange the compounds in each set in order of...Ch. 10 - Prob. 10.23PCh. 10 - The decalinols A and B can be equilibrated using...Ch. 10 - Prob. 10.25PCh. 10 - Select the stronger acid from each pair and...Ch. 10 - Prob. 10.27PCh. 10 - In each equilibrium, label the stronger acid, the...Ch. 10 - Write equations for the reaction of 1-butanol with...Ch. 10 - Write equations for the reaction of 2-butanol with...Ch. 10 - Prob. 10.31PCh. 10 - When (R)-2-butanol is left standing in aqueous...Ch. 10 - Two diastereomeric sets of enantiomers, A/B and...Ch. 10 - Acid-catalyzed dehydration of 3-methyl-2-butanol...Ch. 10 - Show how you might bring about the following...Ch. 10 - Propose a mechanism for the following pinacol...Ch. 10 - Prob. 10.37PCh. 10 - Show how each alcohol or diol can be prepared from...Ch. 10 - Dihydropyran is synthesized by treating...Ch. 10 - Show how to convert propene to each of these...Ch. 10 - Prob. 10.41PCh. 10 - Prob. 10.42PCh. 10 - The tosylate of a primary alcohol normally...Ch. 10 - Prob. 10.44PCh. 10 - Show how to convert cyclohexene to each compound...Ch. 10 - Prob. 10.46PCh. 10 - Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3)...Ch. 10 - Prob. 10.48PCh. 10 - Prob. 10.49PCh. 10 - Prob. 10.50PCh. 10 - Write the products of the following sequences of...Ch. 10 - Alcohols are important for organic synthesis,...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59P
Knowledge Booster
Similar questions
- Draw the structural formula of the products formed when each alkene is treated with one equivalent of NBS in CH2Cl2 in the presence of light.arrow_forwardBoth 1,2-dihydronaphthalene and 1,4-dihydronaphthalene may be selectively hydrogenated to 1,2,3,4-tetrahydronaphthalene.One of these isomers has a heat of hydrogenation of 101 kJ/mol (24.1 kcal/mol), and the heat of hydrogenation of the other is 113 kJ/mol (27.1 kcal/mol). Match the heat of hydrogenation with the appropriate dihydronaphthalene.arrow_forwardSN2 reaction is an example of a nucleophilic substitution reaction. Imagine that 1-iodobutane reacts with 4-methylheptan-1-ol under basic conditions. Draw the structure of the two reactants.arrow_forward
- Use a sheet of paper to answer the following question. Take a picture of your answers and attach to this assignment. n-Pentanol (CH3CH2CH₂CH₂CH₂OH) and 2-methylbutan-2-ol (CH3CH₂C(CH3)2OH) are converted to their corresponding alkyl chorides on being reacted with hydrogen chloride. (a) Write out an equation for each reaction (b) Assign each the appropriate symbol (SN1 or SN2) (c) Write a suitable mechanism for each reactionarrow_forwardDuring an experiment in your chemistry lab, your instructor assigned your group to make a refill of Fehling’s A and Fehling’s B solution and Benedicts solution. Both Fehling’s and Benedict’s solutions are a reagent used to differentiate aldehydes from ketones and used for detecting reducing sugars. Your group was asked to make 120 ml of each solution. Show your complete solution. Preparation of Fehling's solution A:Dissolve 35g of Cu2SO4.7H2O in water and make up to 500mlPreparation of Fehling's solution B:Dissolve 120 g of KOH and 173 g of Sodium Potassium Tartrate (Rochelle salt) in water and make up to 500 mlarrow_forward1. The acid-catalyzed elimination of an alcohol is an equilibrium reaction and requires special reac- tion conditions to favour the formation of the alkene product. What chemical principle controls the amount of alkene product that is produced? Provide two laboratory techniques that can be used to obtain good alkene yields in alcohol elimination reactions.arrow_forward
- In the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl (trityl) ethers to protect the hydroxyl group from reaction with other reagents. Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. (a) Why are triphenylmethyl ethers so readily hydrolyzed by aqueous acid? (b) How might the structure of the triphenylmethyl group be modified to increase or decrease its acid sensitivity?arrow_forwardWhat products would result from the following processes? Write an equation for each reaction. a. 2-Methyl-2-butanol is subjected to controlled oxidation. b. 1-Propanol is heated to 140C in the presence of sulfuric acid. c. 3-Pentanol is subjected to controlled oxidation. d. 3-Pentanol is heated to 180C in the presence of sulfuric acid. e. 1-Hexanol is subjected to an excess of oxidizing agent.arrow_forwardAccount for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid.arrow_forward
- 16-54 Several poisonous plants, including Atropa belladonna, contain the alkaloid atropine. The name “belladonna” (which means “beautiful lady”) probably comes from the fact that Roman women used extracts from this plant to make themselves more attractive. Atropine is widely used by ophthal mologists and optometrists to dilate the pupils for eye examination. Classify the amino group in atropine as primary, secondary, or tertiary. Locate all stereocenters in atropine. Account for the fact that atropine is almost insoluble in water (1 g in 455 mL of cold water) but atropine hydrogen sulfate is very soluble (1 g in 5 mL of cold water). Account for the fact that a dilute aqueous solution of atropine is basic (pH approximately 10.0).arrow_forwardGive IUPAC names for the following substances:arrow_forwardIdentify the most important aldehyde and ketone from Section 14.4 on the basis of amount used, and list at least one characteristic for each that contributes to its usefulness.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
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning