Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 7, Problem 12PP
Practice Problem 7.14
Dehydration of 2-propanol occurs in 14 M
(a) Using curved arrows, write all steps in a mechanism for the dehydration.
(b) Explain the essential role performed in alcohol dehydrations by the acid catalyst. (Hint: Consider what would have to happen if no acid were present.)
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(ii)
(iii)
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Chapter 7 Solutions
Organic Chemistry
Ch. 7 - Prob. 1PPCh. 7 - Prob. 2PPCh. 7 - Prob. 3PPCh. 7 - Prob. 4PPCh. 7 - Practice Problem 7.5
How many stereoisomers are...Ch. 7 - Prob. 6PPCh. 7 - Prob. 7PPCh. 7 - PRACTICE PROBLEM 7.8
Examine Solved Problem 7.3....Ch. 7 - Prob. 9PPCh. 7 - Practice Problem 7.10 When...
Ch. 7 - Practice Problem 7.11
(a) When...Ch. 7 - Practice Problem 7.14
Dehydration of 2-propanol...Ch. 7 - Practice Problem 7.15
Rank the following alcohols...Ch. 7 - Practice Problem 7.16
Acid-catalyzed dehydration...Ch. 7 - Practice Problem 7.17 Acid-catalyzed dehydration...Ch. 7 - Prob. 16PPCh. 7 - Prob. 17PPCh. 7 - Practice Problem 7.20
Show how you might...Ch. 7 - Prob. 19PPCh. 7 - Prob. 20PPCh. 7 - Practice Problem 7.23
Write the structure of...Ch. 7 - Prob. 22PPCh. 7 - Prob. 23PPCh. 7 - Practice Problem 7.26 (a) Devise retrosynthetic...Ch. 7 - Each of the following names is incorrect, Give the...Ch. 7 - Prob. 26PCh. 7 - Prob. 27PCh. 7 - Give the IUPAC names for each of the following:...Ch. 7 - Prob. 29PCh. 7 - Prob. 30PCh. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - 7.54. Outline a synthesis of phenylethyne from...Ch. 7 - Prob. 34PCh. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - 7.35. Write structural formulas for all the...Ch. 7 - 7.47. Starting with an appropriate alkyl halide...Ch. 7 - Arrange the following alcohols in order of their...Ch. 7 - Prob. 41PCh. 7 - Prob. 42PCh. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - 7.49. What is the index of hydrogen deficiency...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - Compounds I and J both have the molecular formula...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - Consider the interconversion of cis-2-butene and...Ch. 7 - Prob. 52PCh. 7 - (a) Using reactions studied in this chapter, show...Ch. 7 - Prob. 54PCh. 7 - Prob. 55PCh. 7 - 1. Write the structure(s) of the major product(s)...Ch. 7 - Prob. 2LGPCh. 7 - (a) Write the structure of the product(s) formed...Ch. 7 - Prob. 4LGPCh. 7 - Prob. 5LGPCh. 7 - 7.1 Which conditions/reagents would you employ to...Ch. 7 - Which of the following names is incorrect? (a)...Ch. 7 - 7.3 Select the major product of the reaction
Ch. 7 - 7.4 Supply the missing reagents.
Ch. 7 - Arrange the following alkenes in order of...Ch. 7 - 7.6 Complete the following synthesis.
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- PRACTICE PROBLEM 8.20 Specify the alkene and reagents needed to synthesize each of the following diols. OH HO- (a) (b) (c) HO. н он HO (racemic) (racemic)arrow_forwardWhich is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolarrow_forwardCan i get help with this problemarrow_forward
- (a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forward4.33 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-Butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol (e) 1-Methylcyclopentanol or cyclohexanol Draw the energy diagrams of an SN1 reaction and an SN2 reaction. Include in your drawing anexample reaction. Identify the rate limiting step and label it as unimolecular or bimolecular.arrow_forwardPractice Problem 7.16 When the compound called isoborneol is heated with 9 M sulfuric acid, the product of the reaction is the compound called camphene and not bornylene, as one might expect. Using models to assist you, write a step-by-step mechanism showing how camphene is formed. HO H,O not heat Isoborneol Camphene Bornylenearrow_forward
- Draw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)arrow_forwardGive reasons for the following :(i) Phenol is more acidic than methanol.(ii) The C—O—H bond angle in alcohols is slightly less than the tetrahedral angle (190°28′).(iii) (CH3)3C—O—CH3 on reaction with HI gives (CH3)3C—I and CH3—OH as the main products and not (CH3)3C—OH and CH3—I.arrow_forwardDraw the structural formula(s) for the major product(s) of each of the following reactions. Unless required, ignore stereochemical details.arrow_forward
- Predict the major products of dehydration catalyzed by sulfuric acid. (a) cyclopentylmethanol (b) 2-methylcyclopentanolarrow_forwardThe hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?arrow_forwardWhen tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether. (a) What happens to the reaction rate if the concentration of ethanol is doubled?arrow_forward
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