Principles of Instrumental Analysis
7th Edition
ISBN: 9781305577213
Author: Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher: Cengage Learning
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Chapter 19, Problem 19.19QAP
Interpretation Introduction
Interpretation:
The 1H NMR spectra for methanol at room temperature and -400C should be sketched.
Concept introduction:
Hydroxyl group in methanol involves in H bonding. But at high temperatures, these hydrogen bonding is weakened and its signal is shielded due to the increase in the rate of intermolecular proton exchange. So at room temperature the two types of H are undetectable in NMR. But at low temperatures, formation of H bonding is encouraged and lowers the rate of proton exchange. So, at low temperatures two types of H are detectable hence, spin-spin coupling can be observed.
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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
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.
Don't used hand raiting
Chapter 19 Solutions
Principles of Instrumental Analysis
Ch. 19 - Prob. 19.1QAPCh. 19 - Prob. 19.2QAPCh. 19 - Prob. 19.3QAPCh. 19 - Prob. 19.4QAPCh. 19 - Prob. 19.5QAPCh. 19 - A nucleus has a spin quantum number of 7/2. How...Ch. 19 - Prob. 19.7QAPCh. 19 - Prob. 19.8QAPCh. 19 - Prob. 19.9QAPCh. 19 - Why is 133C-133C spin-spin splitting not observed...
Ch. 19 - Prob. 19.11QAPCh. 19 - Prob. 19.12QAPCh. 19 - Prob. 19.13QAPCh. 19 - What is a rotating frame of reference?Ch. 19 - How will E for an isolated 13C nucleus compare...Ch. 19 - Prob. 19.16QAPCh. 19 - Prob. 19.17QAPCh. 19 - Prob. 19.18QAPCh. 19 - Prob. 19.19QAPCh. 19 - Prob. 19.20QAPCh. 19 - Prob. 19.21QAPCh. 19 - Prob. 19.22QAPCh. 19 - Prob. 19.23QAPCh. 19 - Prob. 19.24QAPCh. 19 - Prob. 19.25QAPCh. 19 - Prob. 19.26QAPCh. 19 - Prob. 19.27QAPCh. 19 - Prob. 19.28QAPCh. 19 - Prob. 19.29QAPCh. 19 - Prob. 19.30QAPCh. 19 - The proton NMR spectrum in Figure 19.39 is for an...Ch. 19 - The proton NMR spectrum in Figure 19-40 is for a...Ch. 19 - Prob. 19.33QAPCh. 19 - Prob. 19.34QAPCh. 19 - Prob. 19.35QAPCh. 19 - From the proton NMR spectrum in Figure 19-44,...Ch. 19 - From the proton spectrum given in Figure 19-45,...Ch. 19 - Prob. 19.38QAPCh. 19 - Prob. 19.39QAPCh. 19 - Prob. 19.40QAPCh. 19 - Prob. 19.41QAPCh. 19 - Prob. 19.42QAP
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