Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 5, Problem 5.8P
Interpretation Introduction
Interpretation:
Concept introduction:
When the symmetrical alkenes are treated with oxymercuration-demercuration or hydroboration-oxidation then it will lead to same product. In case of unsymmetrical alkenes they give different products on treatment with oxymercuration-demercuration or hydroboration-oxidation.
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Draw the alkene that would react with the reagent given to account for the product formed.
CH3
HCI
CH3 CHCCH,
? +
Či CH3
You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• In cases where there is more than one answer, just draw one.
1. Consider the solubility and boiling point of the following pair of compounds: n-butyl alcohol and diethyl ether. The boiling points for the compounds are 118 °C and 35 °C respectively. The solubility for both compounds is the same (8g/100g water). Explain this observation for (i) boiling point disparity; (ii) solubility similarity
a. H-bonds form in diethyl ether; n-butyl alcohol forms H-bonds in water
b. H-bonds form in n-butyl alcohol; diethyl ether forms H-bonds in water
c. H-bonds in n-butyl alcohol; Both compounds form H-bonds in water
d. Both compounds form H-bonds; Both compounds form H-bonds in water
2. Account for the bond angle differences between (i) H-C-H (109.5°) in methane and H-S-H (90°); H-C-H (109.5°) and H-O-H (107.5°) in water.
a. The H-S-H has two lone pairs; The H-O-H has two lone pairs
b. The H-S-H has no hybridization at p-orbitals; The H-O-H has two lone pairs
c. The H-S-H has two lone pairs; The H-O-H has no hybridization…
Draw the alkene that would react with the reagent given to account for the product formed.
OH
H₂SO4
CH3CH2CCH2CH3
?
+
H₂O
CH2CH3
. You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• In cases where there is more than one answer, just draw one.
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Prob. 5.3PCh. 5 - Prob. 5.4PCh. 5 - Prob. 5.5PCh. 5 - Prob. 5.6PCh. 5 - Prob. 5.7PCh. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Prob. 5.13PCh. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - Prob. 5.27APCh. 5 - Prob. 5.28APCh. 5 - Prob. 5.29APCh. 5 - Prob. 5.30APCh. 5 - Prob. 5.31APCh. 5 - Prob. 5.32APCh. 5 - Prob. 5.33APCh. 5 - Prob. 5.34APCh. 5 - Prob. 5.35APCh. 5 - Prob. 5.36APCh. 5 - Prob. 5.37APCh. 5 - Prob. 5.38APCh. 5 - Prob. 5.39APCh. 5 - Prob. 5.40APCh. 5 - Prob. 5.41APCh. 5 - Prob. 5.42APCh. 5 - Prob. 5.43APCh. 5 - Prob. 5.44APCh. 5 - Prob. 5.45APCh. 5 - Prob. 5.46APCh. 5 - Prob. 5.47APCh. 5 - Prob. 5.48APCh. 5 - Prob. 5.49APCh. 5 - Prob. 5.50APCh. 5 - Prob. 5.51APCh. 5 - Prob. 5.52APCh. 5 - Prob. 5.53APCh. 5 - Prob. 5.54AP
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