Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 3, Problem 16PP
PRACTICE PROBLEM 3.16
Your laboratory instructor gives you a mixture of 4-methylphenol, benzoic acid, and toluene. Assume that you have available common laboratory acids, bases, and solvents and explain how you would proceed to separate this mixture by making use of the solubility differences of its components.
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PRACTICE PROBLEM 2.2
The compounds in each part below have the same (or similar) molecular weights. Which
compound in cach part would you expect to have the higher boiling point? Explain your
answers.
(a)
OH or
(c)
OH or HO
(b) (CHN or
A factor (in addition to polarity and hydrogen bonding) that affects the melting point
of many organic compounds is the compactness and rigidity of their individual molecules.
• Molecules that are symmetrical generally have abnormally high melting points. sert-
Buryl alcohol, for example, has a much higher melting point than the other isomeric
alcohols shown here:
OH
OH
tert-Butyl alcohol
(mp 25 "C)
Butyl alcohol
(mp -00 "C)
Isobutyl alcohol sec-Butyl alcohol
(mp 108 C)
(mp-114 C)
о о
(a) Give the names of reagents and conditions for each of the reactions I and II
Explain a procedure to separate a mixture of the following 3 compounds to 3 separate individual components. May use any organic solvents and reagents. (Part A is first mixture, Part B is second mixture)
First answer (a) then (b)
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 1PPCh. 3 - PRACTICE PROBLEM 3.2
Write equations showing the...Ch. 3 - PRACTICE PROBLEM 3.3 Which of the following are...Ch. 3 - Prob. 4PPCh. 3 - PRACTICE PROBLEM 3.5 Formic acid (HCO2H) has...Ch. 3 - Prob. 6PPCh. 3 - Prob. 7PPCh. 3 - Prob. 8PPCh. 3 - PRACTICE PROBLEM 3.9 Predict the outcome of the...Ch. 3 - Prob. 10PP
Ch. 3 - Prob. 11PPCh. 3 - Prob. 12PPCh. 3 - Prob. 13PPCh. 3 - Prob. 14PPCh. 3 - PRACTICE PROBLEM 3.15 Nitro groups have a large...Ch. 3 - PRACTICE PROBLEM 3.16
Your laboratory instructor...Ch. 3 - Prob. 17PPCh. 3 - Prob. 18PPCh. 3 - Prob. 19PPCh. 3 - What is the conjugate base of each of the...Ch. 3 - List the bases you gave as answers to Problem 3.20...Ch. 3 - 3.22 What is the conjugate acid of each of the...Ch. 3 - List the acids you gave as answers to Problem 3.22...Ch. 3 - Rank the following in order of increasing acidity.Ch. 3 - Without consulting tables, select the stronger...Ch. 3 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - 3.30 What reaction will take place if ethyl...Ch. 3 - 3.31 (a) The of formic acid. What is the? (b)...Ch. 3 - Acid HA has pKa=20; acid HB has pKa=10. (a) Which...Ch. 3 - Prob. 33PCh. 3 - 3.34 (a) Arrange the following compounds in order...Ch. 3 - 3.35 Arrange the following compounds in order of...Ch. 3 - 3.36 Arrange the following in order of increasing...Ch. 3 - Prob. 37PCh. 3 - 3.38 Supply the curved arrows necessary for the...Ch. 3 - Glycine is an amino acid that can be obtained from...Ch. 3 - 3.40 Malonic acid, , is a diprotic acid. The for...Ch. 3 - 3.41 The free-energy change, , for the ionization...Ch. 3 - 3.42 At the enthalpy change, , for the ionization...Ch. 3 - The compound at right has (for obvious reasons)...Ch. 3 - 3.44.
(a) Given the above sequence of...Ch. 3 - Prob. 45PCh. 3 - Prob. 46PCh. 3 - 3.47 As noted in Table 3.1, the of acetone, , is...Ch. 3 - Formamide (HCONH2) has a pKa of approximately 25....Ch. 3 - List all the chemical species likely to be present...Ch. 3 - Prob. 2LGPCh. 3 - Prob. 3LGPCh. 3 - Prob. 4LGP
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