ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
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Textbook Question
Chapter 6.5A, Problem 6.6P
For each pair of compounds, predict which compound has the higher boiling point. Check Table6-2 to see if your prediction was right; then explain why that compound has the higher boiling point.
- a. isopropyl bromide and n-butyl bromide
- b. isopropyl chloride and tert-butyl bromide
- c. 1-bromobutane and 1-chlorobutane
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Question 19
0/2 pts 3
Details
You have a mixture of sodium chloride (NaCl) and potassium chloride (KCl) dissolved in water
and want to separate out the Cl- ions by precipitating them out using silver ions (Ag+). The
chemical equation for the net ionic reaction of NaCl and KCl with silver nitrate, AgNO3, is shown
below.
Ag+(aq) + Cl(aq) → AgCl(s)
The total mass of the NaCl/KCl mixture is 1.299 g. Adding 50.42 mL of 0.381 M solution
precipitates out all of the Cl-.
What are the masses of NaCl and KCl in the mixture?
Atomic masses:
g: Mass of NaCl
g: Mass of KCL
Ag = 107.868 g
mol-
1
Cl = 35.453 g mol-
1
K = 39.098 g mol-
N = 14.007 g mol−1
Na = 22.99 g mol−1
0 = 15.999 g mol
1
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Part 1. Draw monomer units of the following products and draw their reaction mechanism (with arrow pushing)
Polyester fiber
Using a) pthalic anhydride + anhydrous sodium acetate + ethylene glycol
B)pthalic anhydride + anhydrous sodium acetate + glycerol
Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any.
If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers).
If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products.
If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)
Chapter 6 Solutions
ORGANIC CHEMISTRY
Ch. 6.1 - Classify each compound as an alkyl halide, a vinyl...Ch. 6.2 - Give the structures of the following compounds. a....Ch. 6.2 - For each of the following compounds, A. give the...Ch. 6.3E - Prob. 6.4PCh. 6.4 - Prob. 6.5PCh. 6.5A - For each pair of compounds, predict which compound...Ch. 6.5B - Prob. 6.7PCh. 6.6B - Prob. 6.8PCh. 6.6B - The light-initiated reaction of...Ch. 6.6B - Show how free-radical halogenation might be used...
Ch. 6.7 - Prob. 6.11PCh. 6.7 - Prob. 6.12PCh. 6.8 - Prob. 6.13PCh. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15PCh. 6.10A - Prob. 6.16PCh. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18PCh. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20PCh. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23PCh. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25PCh. 6.15 - Prob. 6.26PCh. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28PCh. 6.16 - Prob. 6.29PCh. 6 - Prob. 6.30SPCh. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SPCh. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SPCh. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SPCh. 6 - Prob. 6.38SPCh. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SPCh. 6 - Prob. 6.42SPCh. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SPCh. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SPCh. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SPCh. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SPCh. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SPCh. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SPCh. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SPCh. 6 - Prob. 6.59SP
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