ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Question
Chapter 25, Problem 35DSP
Interpretation Introduction
Interpretation:
The number of acetate and propanoate units are to be determined in the given structure of
Concept Introduction:
An acetate unit contributes two carbon atoms in a synthesis while a propanoate unit contributes three carbon atoms.
In
The methyl carbon atom in propanoate is the beta carbon atom and remains unreacted in the synthesis.
The number of methyl groups indicate the number of propanoate units in the synthesis.
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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
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possible
CH3CH2CH2MgBr
Q10
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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.
Don't used hand raiting
Chapter 25 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
Ch. 25.2 - What fatty acids are produced on hydrolysis of...Ch. 25.3 - Give the structure of the keto acyl-ACP formed...Ch. 25.4 - Prob. 3PCh. 25.4 - Prob. 4PCh. 25.5 - Prob. 5PCh. 25.6 - Write the structural formula and give the IUPAC...Ch. 25.6 - Prob. 7PCh. 25.7 - Locate the isoprene units in each of the...Ch. 25.7 - Prob. 9PCh. 25.9 - Prob. 10P
Ch. 25.9 - Prob. 11PCh. 25.10 - Prob. 12PCh. 25.11 - Prob. 13PCh. 25.11 - Prob. 14PCh. 25.12 - Prob. 15PCh. 25.16 - Prob. 16PCh. 25 - Prob. 17PCh. 25 - Prob. 18PCh. 25 - Prob. 19PCh. 25 - Pyrethrins are a group of naturally occurring...Ch. 25 - Prob. 21PCh. 25 - Prob. 22PCh. 25 - Prob. 23PCh. 25 - Prob. 24PCh. 25 - Prob. 25PCh. 25 - Prob. 26PCh. 25 - Prob. 27PCh. 25 - Prob. 28PCh. 25 - A synthesis of triacylglycerols has been described...Ch. 25 - Prob. 30PCh. 25 - Prob. 31PCh. 25 - Prob. 32PCh. 25 - Prob. 33DSPCh. 25 - Prob. 34DSPCh. 25 - Prob. 35DSPCh. 25 - Prob. 36DSPCh. 25 - Prob. 37DSPCh. 25 - Prob. 38DSP
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