Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 11.7B, Problem 11.14P
Show how you would use a simple chemical test to distinguish between the following pairs of compounds. Tell what you would observe with each compound.
- a. isopropyl alcohol and tert-butyl alcohol
- b. isopropyl alcohol and butan-2-one, CH3COCH2CH3
- c. hexan-1-ol and cyclohexanol
- d. allyl alcohol and propan-1-ol
- e. butan-2-one and tert-butyl alcohol
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CH2
H3C
H3C
COOH
Reagents
e. PB13
f. NaCN then H3O*
g. NBS, CCI4
h. CrO3, H2SO4
а.
HBr
b. Mg, ether
c. CO2, ether then H3O*
d. BH3, THF then H2O2, OH"
Reagents
a. C6H5CHO
b. NaOH, ethanol
h. BrCH2CH=CH2
i.
Na* OEt, ethanol
j. Br2, H*
k. K* t-BuO
c. Pyrrolidine, cat. H*
d. H2C=CHCN
e. H3O*
f.
I. CH2(CO2ET)2
-CH2CH2CN
LDA
m. heat
g. ELOC(=0)CO2ET
Select reagents from the table to synthesize this compound from cyclopentanone.
Enter the letters of the chosen reagents, in the order that you wish to use them, without spaces or punctuation (i.e. geda).
F.
OH
1. Write the IUPAC names for these alcohols.
A. CH,OHCH(CHa)CH,OH
В.
CH3
G.
CICH2CHCHCH3
но
OH
Н.
C.
но
OH
CI
1.
HO
D.
OH
J.
ÇH3
он
CHCHCHCH(CHз)2
E.
CH2CH3
OH
K.
OH
Br
CH3
OH
Page 1
Chapter 11 Solutions
Organic Chemistry (9th Edition)
Ch. 11.1 - Prob. 11.1PCh. 11.2C - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.3 - Prob. 11.4PCh. 11.3 - Prob. 11.5PCh. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...
Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
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