Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
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Textbook Question
Chapter 13.7, Problem 13.5P
Draw the integral trace expected for the NMR spectrum of tert-butyl acetoacetate, shown in Figure13-17.
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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 13 Solutions
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
Ch. 13.5A - In a 300-MHz spectrometer, the protons in...Ch. 13.5B - Prob. 13.2PCh. 13.6 - Determine the number of different kinds of protons...Ch. 13.6 - Prob. 13.4PCh. 13.7 - Draw the integral trace expected for the NMR...Ch. 13.7 - Prob. 13.6PCh. 13.8C - Draw the NMR spectra you would expect for the...Ch. 13.8D - Draw the NMR spectra you expect for the following...Ch. 13.8D - a. Assign protons to the peaks in the NMR spectrum...Ch. 13.8D - Prob. 13.10P
Ch. 13.8D - Two spectra are shown. Propose a structure that...Ch. 13.9 - Prob. 13.12PCh. 13.9 - The spectrum of trans-hex-2-enoic acid follows. a....Ch. 13.9 - Prob. 13.14PCh. 13.9 - Prob. 13.15PCh. 13.10 - Prob. 13.16PCh. 13.10 - If the imaginary replacement of either of two...Ch. 13.10 - Predict the theoretical number of different NMR...Ch. 13.11B - Prob. 13.19PCh. 13.11B - Prob. 13.20PCh. 13.11B - Prob. 13.21PCh. 13.11B - Prob. 13.22PCh. 13.11B - Prob. 13.23PCh. 13.11B - Prob. 13.24PCh. 13.12E - Draw the expected broadband-decoupled 13 C N M R...Ch. 13.12E - a. Show which carbon atoms correspond with which...Ch. 13.12E - Repeat Problem13-25, sketching the...Ch. 13.12F - Prob. 13.28PCh. 13.13 - A bottle of allyl bromide was found to contain a...Ch. 13.13 - A laboratory student was converting cyclohexanol...Ch. 13.14 - Sets of spectra are given for two compounds. For...Ch. 13 - An unknown compound has the molecular formula C 9...Ch. 13 - Prob. 13.34SPCh. 13 - Predict the approximate chemical shifts of the...Ch. 13 - Prob. 13.36SPCh. 13 - Prob. 13.37SPCh. 13 - Prob. 13.38SPCh. 13 - Prob. 13.39SPCh. 13 - Prob. 13.40SPCh. 13 - For each compound shown below. 1. sketch the 13 C...Ch. 13 - Prob. 13.42SPCh. 13 - Prob. 13.43SPCh. 13 - Prob. 13.44SPCh. 13 - Prob. 13.45SPCh. 13 - Prob. 13.46SPCh. 13 - A compound was isolated as a minor constituent in...Ch. 13 - Prob. 13.48SPCh. 13 - The three isomers of dimethylbenzene are commonly...Ch. 13 - a. Draw all six isomers of formula C 4 H 8...Ch. 13 - Prob. 13.51SPCh. 13 - Hexamethylbenzene undergoes free-radical...Ch. 13 - Each of these four structures has molecular...Ch. 13 - Prob. 13.54SPCh. 13 - Phenyl Grignard reagent adds to 2-methylpropanal...Ch. 13 - Prob. 13.56SP
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- A DEPT NMR spectrum is shown for a molecule with the molecular formula of C5H12O. Draw the structure that best fits this data. 200 180 160 140 120 100 一盆 00 40 8- 20 ppm 0 Qarrow_forwardDon't used hand raitingarrow_forwardShown below is the major resonance structure for a molecule. Draw the second best resonance structure of the molecule. Include all non-zero formal charges. H. H. +N=C H H H Cl: Click and drag to start drawing a structure. : ? g B S olo Ar B Karrow_forward
- Don't used hand raitingarrow_forwardS Shown below is the major resonance structure for a molecule. Draw the second best resonance structure of the molecule. Include all non-zero formal charges. H H = HIN: H C. :0 H /\ H H Click and drag to start drawing a structure. ×arrow_forwardPlease help me figure out these calculation and what should be plotted. These are notes for my chemistry class.arrow_forward
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