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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Textbook Question
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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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
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ChemDoodle
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1. Consider the solubility and boiling point of the following pair of compounds: n-butyl alcohol and diethyl ether. The boiling points for the compounds are 118 °C and 35 °C respectively. The solubility for both compounds is the same (8g/100g water). Explain this observation for (i) boiling point disparity; (ii) solubility similarity
a. H-bonds form in diethyl ether; n-butyl alcohol forms H-bonds in water
b. H-bonds form in n-butyl alcohol; diethyl ether forms H-bonds in water
c. H-bonds in n-butyl alcohol; Both compounds form H-bonds in water
d. Both compounds form H-bonds; Both compounds form H-bonds in water
2. Account for the bond angle differences between (i) H-C-H (109.5°) in methane and H-S-H (90°); H-C-H (109.5°) and H-O-H (107.5°) in water.
a. The H-S-H has two lone pairs; The H-O-H has two lone pairs
b. The H-S-H has no hybridization at p-orbitals; The H-O-H has two lone pairs
c. The H-S-H has two lone pairs; The H-O-H has no hybridization…
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. CH3 CH3CHCH₂CH₂CH₂OH • 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_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_forwardGive at least 3 features in the structure of an alkene.arrow_forward
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