ORGANIC CHEMISTRY 2-SEMESTER-ACCESS
4th Edition
ISBN: 9781119659532
Author: Klein
Publisher: WILEY
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Chapter 1.13, Problem 31ATS
Interpretation Introduction
Interpretation: The compound that has higher boiling point should be identified amongst product 3 and 4.
Concept Introduction: The temperature at which transition of a substance takes place from liquid to gaseous state is said to be its boiling point. At boiling point, the vapor pressure and applied pressure on the liquid become equal. There is a direct relationship between the interaction present in molecule and the boiling point of the molecule. The molecule that has stronger interaction between its atoms/molecules possess higher boiling point and vice-versa.
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In an experiment, triphenylmethanol is prepared using the Grignard reaction. The Grignard reaction involves preparation and reaction of a very nucleophilic organo-magnesium compound. The Grignard reagent is very reactive and is easily destroyed by reaction with atmospheric water, oxygen, or carbon dioxide. The Grignard reagent must be prepared under strict anhydrous conditions (dry glassware, dry solvent). The volative solvent, diethyl ether, helps to prevent oxygen or carbon dioxide from entering the reaction vessel. Reaction of bromobenzene with magnesium in ether produces phenylmagnesium bromide. This Grignard reagent then reacts with methyl benzoate to produce the corresponding alkoxide. Reaction of the alkoxide with aqueous acid then produces the alcohol.
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In an experiment, triphenylmethanol is prepared using the Grignard reaction. The Grignard reaction involves preparation and reaction of a very nucleophilic organo-magnesium compound. The Grignard reagent is very reactive and is easily destroyed by reaction with atmospheric water, oxygen, or carbon dioxide. The Grignard reagent must be prepared under strict anhydrous conditions (dry glassware, dry solvent). The volative solvent, diethyl ether, helps to prevent oxygen or carbon dioxide from entering the reaction vessel. Reaction of bromobenzene with magnesium in ether produces phenylmagnesium bromide. This Grignard reagent then reacts with methyl benzoate to produce the corresponding alkoxide. Reaction of the alkoxide with aqueous acid then produces the alcohol.
Why is it unwise to begin addition of the solution of carbonyl compound to the Grignard reagent before the latter has cooled to room temperature?
4) Multistriatin, one of the pheremones of the elm bark beetle, is a volatile
compound released by a virgin female beetle when she has found a good food
source - an elm tree. Male beetles, which carry the Dutch elm disease fungus,
are attracted by the pheromone; the tree becomes infected with the fungus and
soon dies. Multistriatin is used to trap the beetles, but the amount in beetles
is so miniscule that the compound must be synthesized. The following synthesis
of multistriatin uses only chemistry that we have seen in Chem 348.
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HO
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type
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hint: anhydrous cond
CH3
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H
type
type
HO
CH3
H
H
type
CH 3
H
Multistriatin
Multistriatin
Chapter 1 Solutions
ORGANIC CHEMISTRY 2-SEMESTER-ACCESS
Ch. 1.2 - Prob. 1LTSCh. 1.2 - Prob. 2ATSCh. 1.2 - Prob. 2LTSCh. 1.3 - Prob. 3LTSCh. 1.3 - Prob. 4PTSCh. 1.3 - Prob. 5PTSCh. 1.4 - Prob. 4LTSCh. 1.4 - Prob. 7PTSCh. 1.4 - Prob. 8PTSCh. 1.4 - Prob. 9ATS
Ch. 1.5 - Prob. 5LTSCh. 1.5 - Prob. 10PTSCh. 1.5 - Prob. 11ATSCh. 1.5 - Prob. 12ATSCh. 1.6 - Prob. 6LTSCh. 1.6 - Prob. 14ATSCh. 1.7 - Prob. 7LTSCh. 1.7 - Prob. 17ATSCh. 1.10 - Prob. 18CCCh. 1.10 - Prob. 20CCCh. 1.10 - Prob. 8LTSCh. 1.10 - Prob. 21PTSCh. 1.10 - Nemotin is a compound that was first isolated from...Ch. 1.10 - Prob. 23CCCh. 1.11 - Prob. 9LTSCh. 1.11 - Prob. 24PTSCh. 1.11 - Prob. 25PTSCh. 1.11 - Prob. 26PTSCh. 1.11 - Prob. 27ATSCh. 1.12 - Prob. 10LTSCh. 1.12 - Prob. 29ATSCh. 1.13 - Prob. 11LTSCh. 1.13 - Prob. 31ATSCh. 1 - Prob. 32PPCh. 1 - Prob. 33PPCh. 1 - Prob. 34PPCh. 1 - Prob. 35PPCh. 1 - Prob. 36PPCh. 1 - Prob. 37PPCh. 1 - Prob. 38PPCh. 1 - Prob. 39PPCh. 1 - Prob. 40PPCh. 1 - Prob. 41PPCh. 1 - Prob. 42PPCh. 1 - Prob. 44PPCh. 1 - Prob. 45PPCh. 1 - Prob. 46PPCh. 1 - Prob. 47PPCh. 1 - Prob. 48PPCh. 1 - Prob. 49PPCh. 1 - Prob. 50PPCh. 1 - Prob. 51PPCh. 1 - Prob. 52PPCh. 1 - Prob. 53PPCh. 1 - Prob. 54PPCh. 1 - Nicotine is an addictive substance found in...Ch. 1 - Prob. 56PPCh. 1 - Prob. 57PPCh. 1 - Prob. 59PPCh. 1 - Prob. 63ASPCh. 1 - Prob. 64ASPCh. 1 - Prob. 66ASPCh. 1 - Prob. 69ASPCh. 1 - Prob. 71ASPCh. 1 - Prob. 72ASPCh. 1 - Prob. 75IP
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