Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 19, Problem 19.50SP
Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.
- a. pentan-1-
amine - b. N-methylbutan-1-amine
- c. N-ethyl-N-propylbutan-2-amine
- d. N-benzylpropan-1-amine
- e. 3-propylaniline
- f. 4-isobutylaniline
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By means of a series of equations outline a method for carrying out the ff. conversions. You may use
reagents you wish. More than one step maybe required.
a. acetylene
b. cyclohexanone
c. ethyl bromide
d. benzene
athanol
+methylcyclohexanol
acetaldehyde
+phenyl ethanol
B-ethyl-3-pentanol
tyclopentanone
2-суano-2-pentanol
benzyl alcohol
2-butanone-semicarbazone
е. 3-рentanol
f. cyclopentene
g. 2-pentanol
h. benzene
i. 2-butanol
Materials
• 1-butanol
• 2-butanol
• 2-methyl-2-propanol
• 3 mol/L H2SO4 (aq)
• 3 mol/L NaOH
• 0.01 mol/L KMNO4
• concentrated (12 mol/L) HCl (aq) for demonstration use only
• distilled water
• 10 mL graduated cylinders or graduated medicine droppers
• test tubes
• test-tube rack
Procedure
Part 1: The comparison of three isomeric alcohols reactions with potassium permanganate
1. Construct an observation table with the following headings.
Alcohol
Observations at 1 minute
Observations at 5 mins
1-Butanol
2-Butanol
2-Methylpropanol
1. In the reactions involving the three isomeric alcohols with the formula C4H9OH, describewhat each of the following tests showed about reactivity of the -OH group and reactions of 1°,2°, and 3° alcohols.• the test with neutral KMnO4• the test with concentrated HCl2. Predict how the fourth alcohol with the formula C4H10O would react if tested with:• 0.01 M KMnO4• concentrated HCl at room temperatureExtend FurtherUse your observations of the solutions formed in the previous experiments and yourunderstanding of alcohols to complete a table like the one shown below. Research the meltingand boiling points to verify your answers.
Chapter 19 Solutions
Organic Chemistry (9th Edition)
Ch. 19.2A - Prob. 19.1PCh. 19.2B - Prob. 19.2PCh. 19.2B - Give correct names for the following amines:Ch. 19.3 - Prob. 19.4PCh. 19.4 - Prob. 19.5PCh. 19.6 - Rank each set of compounds in order of increasing...Ch. 19.8A - Prob. 19.7PCh. 19.8C - Prob. 19.8PCh. 19.8C - Prob. 19.9PCh. 19.8D - a. Show how fragmentation occurs to give the base...
Ch. 19.10B - Propose a mechanism for nitration of pyridine at...Ch. 19.10B - Prob. 19.12PCh. 19.10C - Prob. 19.13PCh. 19.10C - Prob. 19.14PCh. 19.11 - Propose a mechanism to show the individual...Ch. 19.11 - Prob. 19.16PCh. 19.12 - Give the products expected from the following...Ch. 19.13 - Prob. 19.18PCh. 19.13 - Prob. 19.19PCh. 19.14 - Prob. 19.20PCh. 19.15 - Prob. 19.21PCh. 19.15 - Prob. 19.22PCh. 19.16 - Prob. 19.23PCh. 19.17 - Prob. 19.24PCh. 19.17 - Prob. 19.25PCh. 19.18 - Prob. 19.26PCh. 19.19 - Prob. 19.27PCh. 19.20A - Addition of one equivalent of ammonia to...Ch. 19.20A - Prob. 19.29PCh. 19.20B - Show how you would accomplish the following...Ch. 19.20C - Prob. 19.31PCh. 19 - For each compound, 1. classify the...Ch. 19 - Prob. 19.33SPCh. 19 - Within each structure, rank the indicated...Ch. 19 - In each pair of compounds, select the stronger...Ch. 19 - Which of the following compounds are capable of...Ch. 19 - Complete the following proposed acid-base...Ch. 19 - Predict the products of the following reactions:...Ch. 19 - Prob. 19.39SPCh. 19 - Show how m-toluidine can be converted to the...Ch. 19 - The mass spectrum of tert-butylamine follows shows...Ch. 19 - Prob. 19.42SPCh. 19 - The following drugs are synthesized using the...Ch. 19 - Prob. 19.44SPCh. 19 - Synthesize from benzene. (Hint: All of these...Ch. 19 - Propose mechanisms for the following reactions.Ch. 19 - Prob. 19.47SPCh. 19 - Prob. 19.48SPCh. 19 - Prob. 19.49SPCh. 19 - Show how you can synthesize the following...Ch. 19 - Prob. 19.51SPCh. 19 - The alkaloid coniine has been isolated from...Ch. 19 - A chemist is summoned to an abandoned...Ch. 19 - Pyrrole undergoes electrophilic aromatic...Ch. 19 - Prob. 19.55SPCh. 19 - Prob. 19.56SPCh. 19 - An unknown compound shows a weak molecular ion at...Ch. 19 - A compound of formula C11H16N2 gives the IR,...Ch. 19 - (A true story.) A drug user responded to an ad...Ch. 19 - Prob. 19.60SPCh. 19 - Prob. 19.61SPCh. 19 - Prob. 19.62SPCh. 19 - Prob. 19.63SPCh. 19 - Prob. 19.64SPCh. 19 - Prob. 19.65SP
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