Organic Chemistry, Books a la Carte Edition (9th Edition)
9th Edition
ISBN: 9780134160382
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 2.7, Problem 2.10P
Write equations for the following acid-base reactions Use the information in Table 2-2 or Appendix 4 to predict whether the equilibrium will favor the reactants or the products.
- a. HCOOH + −CN
- b. CH3COO− + CH3OH
- c. (CH3)2CHOH + NaNH2
- d. NaOCH3 + HCN
- e. HCI + CH3CH2OH
- f. H3O+ + CH3O−
SOLUTION
to (a): Cyanide is the conjugate base of HCN. It can accept a proton from formic acid:
Reading from Table 2-2 formic acid (pKa = 3.76) is a stronger acid than HCN (pKa = 9 22), and cyanide is a stronger base than formate. The products (weaker acid and base) are favored.
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Experiment:
Each team will be provided with 5g of a mixture of acetanilide and salicylic acid. You will divide it into three 1.5 g portions in separate 125 mL Erlenmeyer flasks savıng some for melting point analysis. Dissolve the mixture in each flask in ~60mL of DI water by heating to boiling on a hotplate. Take the flasks off the hotplate once you have a clear solution and let them stand on the bench top for 5 mins and then allow them to cool as described below.
Sample A-Let the first sample cool slowly to room temperature by letting it stand on your lab bench, with occasional stirring to promote crystallization.
Sample B-Cool the second sample 1n a tap-water bath to 10-15 °C
Sample C-Cool the third sample in an ice-bath to 0-2 °C
Results:
weight after recrystalization and melting point temp.
A=0.624g,102-115°
B=0.765g, 80-105°
C=1.135g, 77-108
What is the percent yield of A,B, and C.
Rel. Intensity
Q
1. Which one of the following is true of the compound
whose mass spectrum is shown
here? Explain how you decided.
100
a) It contains chlorine.
b) It contains bromine.
c) It contains neither chlorine nor bromine.
80-
60-
40-
20-
0.0
0.0
TT
40
80
120
160
m/z
2. Using the Table of IR Absorptions how could you
distinguish between these two
compounds in the IR?
What absorbance would one compound have that the
other compound does not?
HO
CI
Illustrate reaction mechanisms of
alkenes with water in the presence of
H2SO4, detailing each step of the
process. Please show steps of
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#1
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Chapter 2 Solutions
Organic Chemistry, Books a la Carte Edition (9th Edition)
Ch. 2.1A - Prob. 2.1PCh. 2.1B - The NF bond is more polar than the NH bond: but...Ch. 2.1B - For each of the following compounds 1. Draw the...Ch. 2.1B - Two isomers of 1,2-dichloroethene are known One...Ch. 2.2C - Prob. 2.5PCh. 2.2C - Prob. 2.6PCh. 2.3 - Prob. 2.7PCh. 2.4 - Calculate the pH of the following solutions a....Ch. 2.6A - Ammonia appears in Table 2-2 as both an acid and a...Ch. 2.7 - Write equations for the following acid-base...
Ch. 2.7 - Ethanol, methylamine. and acetic acid are all...Ch. 2.8 - Prob. 2.12PCh. 2.10 - Write equations for the following acid-base...Ch. 2.10 - Rank the following acids in decreasing order of...Ch. 2.11 - Prob. 2.15PCh. 2.11 - Prob. 2.16PCh. 2.11 - Consider each pair of bases and explain which one...Ch. 2.12 - Which is a stronger base ethoxide ion or acetate...Ch. 2.12 - Prob. 2.19PCh. 2.12 - Prob. 2.20PCh. 2.12 - Prob. 2.21PCh. 2.12 - Choose the more basic member of each pair of...Ch. 2.14 - Prob. 2.23PCh. 2.15D - Classify the following hydrocarbons and draw a...Ch. 2.16D - Prob. 2.25PCh. 2.17C - Draw a Lewis structure and classify each of the...Ch. 2.17C - Circle the functional groups in the following...Ch. 2 - The CN triple bond in acetonitrile has a dipole...Ch. 2 - Prob. 2.29SPCh. 2 - Sulfur dioxide has a dipole moment of 1.60 D....Ch. 2 - Which of the following pure compounds can form...Ch. 2 - Predict which member of each pair is more soluble...Ch. 2 - Prob. 2.33SPCh. 2 - Prob. 2.34SPCh. 2 - Predict which compound in each pair has the higher...Ch. 2 - All of the following compounds can react as acids...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - The Ka of phenylacetic acid is 5 2 105, and the...Ch. 2 - The following compound can become protonated on...Ch. 2 - The following compounds are listed in increasing...Ch. 2 - Prob. 2.42SPCh. 2 - Prob. 2.43SPCh. 2 - Compare the relative acidity of 1-molar aqueous...Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - The following compounds can all react as bases. a....Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - Prob. 2.48SPCh. 2 - Methyllithium (CH3Li) is often used as a base in...Ch. 2 - Label the reactants in these acid-base reactions...Ch. 2 - In each reaction, label the reactants as Lewis...Ch. 2 - Prob. 2.52SPCh. 2 - Each of these compounds can react as a nucleophile...Ch. 2 - Prob. 2.54SPCh. 2 - Give a definition and an example for each class of...Ch. 2 - Circle the functional groups in the following...Ch. 2 - Prob. 2.57SP
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