Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 4, Problem 4.35AP
The sec-butyl cation can react as both a Brønsted-Lowry acid (a proton donor) and a Lewis acid (an electron pair acceptor) in the presence of a water–sulfuric acid mixture. In each case, however, the product is different. The two reactions are as follows:
- (a) In which reaction(s) does this cation react as a Lewis acid? In which reaction(s) does it react as a Brønsted-Lowry acid?
- (b) Write Lewis structures for reactants and products and show by the use of curved arrows how each reaction occurs.
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Experiment 27 hates & Mechanisms of Reations
Method I visual Clock Reaction
A. Concentration effects on reaction Rates
Iodine
Run [I] mol/L [S₂082] | Time
mo/L
(SCC)
0.04 54.7
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1/ Time Temp Log [ ] 13,20] (time)
/ [I] 199
20.06
23.0
30.04 0.04
0.04 80.0
22.8
45
40.02
0.04 79.0
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22.4
60-080-02 95.0
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(15 pts) Consider the molecule B2H6. Generate a molecular orbital diagram but this
time using a different approach that draws on your knowledge and ability to put
concepts together. First use VSEPR or some other method to make sure you know
the ground state structure of the molecule. Next, generate an MO diagram for BH2.
Sketch the highest occupied and lowest unoccupied MOs of the BH2 fragment.
These are called frontier orbitals. Now use these frontier orbitals as your basis set
for producing LGO's for B2H6. Since the BH2 frontier orbitals become the LGOS,
you will have to think about what is in the middle of the molecule and treat its basis
as well. Do you arrive at the same qualitative MO diagram as is discussed in the
book? Sketch the new highest occupied and lowest unoccupied MOs for the
molecule (B2H6).
Q8: Propose an efficient synthesis of cyclopentene from cyclopentane.
Chapter 4 Solutions
Organic Chemistry, Loose-leaf Version
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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