Experimental Organic Chemistry: A Miniscale & Microscale Approach (Cengage Learning Laboratory Series for Organic Chemistry)
6th Edition
ISBN: 9781305080461
Author: John C. Gilbert, Stephen F. Martin
Publisher: Brooks Cole
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Question
Chapter 9.3, Problem 8E
Interpretation Introduction
Interpretation: In the free-radical chain bromination reaction, the six given hydrocarbons should be arranged in increasing order.
Concept introduction:
Free radicals are uncharged molecules having an unpaired valence electron.
These are typically highly reactive and short-lived molecules.
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Solution
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Use retrosynthetic analysis to suggest two paths to synthesize 2-methyl-3-hexanol using the Grignard reaction. (Click and drag
the appropriate image to the correct position in the reactions.)
Route 1
Aldehyde 1
or
+98
Aldehyde 2
Route 2
Q6
+100
Solved in 1 attempt
Q7
+95
Solved in 2 attempts
Q8
+98
Unlimited attempts
possible
+
+
Grignard 1
OH
H3O+
Grignard 2
Answer Bank
Q9
+90
MgBr
Unlimited attempts
possible
CH3CH2CH2MgBr
Q10
Unlimited attempts
Q11
?
?
+100
in 1 attempt
2-methyl-3-hexanol
CH3CH2MgBr
H
H
о
H
Attempt 3
2) (4 pt) After the reaction was completed, the student collected the following data. Crude
product data is the data collected after the reaction is finished, but before the product
is purified. "Pure" product data is the data collected after attempted purification using
recrystallization.
Student B's data:
Crude product data
"Pure"
product data
after
recrystallization
Crude mass: 0.93 g grey solid
Crude mp: 96-106 °C
Crude % yield:
Pure mass: 0.39 g white solid
Pure mp: 111-113 °C
Pure % yield:
a) Calculate the crude and pure percent yields for the student's reaction.
b) Summarize what is indicated by the crude and pure melting points.
Chapter 9 Solutions
Experimental Organic Chemistry: A Miniscale & Microscale Approach (Cengage Learning Laboratory Series for Organic Chemistry)
Ch. 9.2 - Prob. 1ECh. 9.2 - Prob. 2ECh. 9.2 - Prob. 3ECh. 9.2 - Prob. 4ECh. 9.2 - Prob. 5ECh. 9.2 - Prob. 6ECh. 9.2 - Prob. 7ECh. 9.2 - Prob. 8ECh. 9.2 - Prob. 9ECh. 9.2 - Prob. 10E
Ch. 9.2 - Prob. 11ECh. 9.2 - Prob. 12ECh. 9.2 - Prob. 13ECh. 9.2 - Prob. 14ECh. 9.2 - Prob. 15ECh. 9.2 - Prob. 16ECh. 9.2 - Prob. 17ECh. 9.2 - Prob. 18ECh. 9.2 - Prob. 19ECh. 9.2 - Prob. 20ECh. 9.2 - Prob. 21ECh. 9.2 - Prob. 22ECh. 9.2 - Prob. 23ECh. 9.2 - Prob. 24ECh. 9.3 - Prob. 1ECh. 9.3 - Prob. 2ECh. 9.3 - Prob. 3ECh. 9.3 - Prob. 4ECh. 9.3 - Prob. 5ECh. 9.3 - Prob. 6ECh. 9.3 - Prob. 7ECh. 9.3 - Prob. 8ECh. 9.3 - Prob. 9ECh. 9.3 - Prob. 10ECh. 9.3 - Prob. 11ECh. 9.3 - Prob. 12ECh. 9.3 - Prob. 13ECh. 9.3 - Prob. 14E
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