Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 4.2, Problem 4.4P
Write an equation to show the proton transfer between each
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4-methyl-3-hexanol was prepared by reacting an alkene with either hydroboration-oxidation or oxymercuration-reduction.
Draw the structure of the alkene that was used to prepare the alcohol in highest yield.
• You do not have to consider stereochemistry.
• Indicate the method of preparation by drawing either BH3 (for
. If there is more than one alkene that can be used for a given method, draw all of them.
If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method.
Separate structures with + signs from the drop-down menu.
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ChemDoodle
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hydroboration-oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher.
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1. 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.
2-methyl-2-hexanol was prepared by reacting an alkene with either hydroboration-oxidation or oxymercuration-reduction.
Draw the structure of the alkene that was used to prepare the alcohol in highest yield.
• You do not have to consider stereochemistry.
• Indicate the method of preparation by drawing either BH3 (for hydroboration-oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher.
• If there is more than one alkene that can be used for a given method, draw all of them.
• If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method.
• Separate structures with + signs from the drop-down menu.
*9⁹-85
?
ChemDoodle
Sn [F
Chapter 4 Solutions
Organic Chemistry
Ch. 4.2 - For each conjugate acid-base pair, identify the...Ch. 4.2 - Write these reactions as proton-transfer...Ch. 4.2 - Following is a structural formula for guanidine,...Ch. 4.2 - Write an equation to show the proton transfer...Ch. 4.3 - For each value of Ka, calculate the corresponding...Ch. 4.4 - Predict the position of equilibrium and calculate...Ch. 4.5 - Calculate Keq for a reaction with G0 = 17.1 kJ/mol...Ch. 4.6 - Acid-Base Equilibria Many factors contribute to...Ch. 4.6 - What is the relative trend in acidity and pKa of...Ch. 4.7 - Write an equation for the reaction between each...
Ch. 4 - For each conjugate acid-base pair, identify the...Ch. 4 - Complete a net ionic equation for each...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Prob. 4.12PCh. 4 - In acetic acid, CH3COOH, the OH hydrogen is more...Ch. 4 - Which has the larger numerical value? (a) The pKa...Ch. 4 - In each pair, select the stronger acid. (a)...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - If the G for a reaction is 4.5 kcal/mol at 298 K,...Ch. 4 - Calculate the Keq for the following reactions from...Ch. 4 - Prob. 4.20PCh. 4 - Answer true or false to the following statements...Ch. 4 - In each of the following three reaction coordinate...Ch. 4 - The acid-base chemistry reaction of barium...Ch. 4 - Unless under pressure, carbonic acid (H2CO3) in...Ch. 4 - Prob. 4.25PCh. 4 - Acetic acid, CH3COOH, is a weak organic acid, pKa...Ch. 4 - Benzoic acid, C6H5COOH (pKa 4.19), is only...Ch. 4 - Prob. 4.28PCh. 4 - One way to determine the predominant species at...Ch. 4 - Will acetylene react with sodium hydride according...Ch. 4 - Prob. 4.31PCh. 4 - For each equation, label the Lewis acid and the...Ch. 4 - Complete the equation for the reaction between...Ch. 4 - Each of these reactions can be written as a Lewis...Ch. 4 - The sec-butyl cation can react as both a...Ch. 4 - Prob. 4.36APCh. 4 - Prob. 4.37APCh. 4 - Prob. 4.38APCh. 4 - Explain why the hydronium ion, H3O+, is the...Ch. 4 - What is the strongest base that can exist in...Ch. 4 - Prob. 4.42APCh. 4 - Prob. 4.43APCh. 4 - Methyl isocyanate, CH3N=C=O, is used in the...Ch. 4 - Offer an explanation for the following...Ch. 4 - Prob. 4.46APCh. 4 - Alcohols (Chapter 10) are weak organic acids, pKa...Ch. 4 - As we shall see in Chapter 19, hydrogens on a...Ch. 4 - 2,4-Pentanedione is a considerably stronger acid...Ch. 4 - Write an equation for the acid-base reaction...Ch. 4 - Prob. 4.51APCh. 4 - Prob. 4.52APCh. 4 - Prob. 4.53APCh. 4 - Following is a structural formula for imidazole, a...
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- Draw a structural formula for the alkene you would use to prepare the alcohol shown by hydroboration/oxidation. H3C CH3 CH3CHCCH3 ОН You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forwardWhen bromine is added to two beakers, one containing phenyl isopropyl ether and the other containing cyclohexene, the bromine color in both beakers disappears. What observation could you make while performing this test that would allow you to distinguish the alkene from the aryl ether?arrow_forward2-methyl-2-hexanol was prepared by reacting an alkene with either hydroboration- oxidation or oxymercuration-reduction. Draw the structure of the alkene that was used to prepare the alcohol in highest yield. You do not have to consider stereochemistry. • Indicate the method of preparation by drawing either BH3 (for hydroboration- oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher. • If there is more than one alkene that can be used for a given method, draw all of them. • If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method. Separate structures with + signs from the drop-down menu. ? ChemDoodleⓇ ⒸO [F ▼ [ ] در >arrow_forward
- Write structural formulas for all ketones with the molecular formula C6H12O and give each its IUPAC name. Which of these ketones are chiral?arrow_forwardPlease don't provide handwriting solutionarrow_forwardAnswer both Questions below: Describe giving reagents and reaction conditions, how B may be converted into the compound below The enthalpies of formation of B and C are -52KJ/mol and -156KJ/mol respectively. Calculate the enthalpy of hydrogenation of B, giving your reasoning.arrow_forward
- We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation? (a) the Cr in chromic acid (b) the Cl in sodium hypochlorite (c) the S in the Swern oxidationarrow_forwardWrite the structural formula and name of the organic product for the reaction between an alkyne and an alkyl halide. 1. NANH, CH,CH, CCH → product 2. СH, CH,Br The alkyne group is shown, and should be entered, as CC, without the triple bond. Formatting counts. Enter C before the associated H atoms, and subscript numbers (e.g., CH,CH, CH, OCHCHCH,). product structural formula: CH,CH,CCCH,CH,CH, product name: pent-2-yne Incorrect Incorrectarrow_forwardGive 5 differences of Terminal alkenes and internal alkenesarrow_forward
- The reduction of a certain alkene gave 2-methylbutane. It also gave acetic acid (CH3CO2H) as one of the products when treated with hot basic KMnO4 followed by acidification. Give the IUPAC name of this alkene.arrow_forward2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.arrow_forwardSuppose the alkene in the drawing area below is put in strong acid solution, for example a solution of HBr. Highlight each carbon that might become protonated to form a carbocation intermediate. (The carbocation intermediate might then react with something else to form a final product.) سعدarrow_forward
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