Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 14.5, Problem 4P
identify the most shielded and least shielded protons in
(a)
(b)
(c)
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Consider the reaction of a propanoate ester with hydroxide ion shown below. A
series of four alcohol leaving groups were tested to determine which would be the
best leaving group.
Based on the pKa values of the alcohols, predict which alcohol would produce the
fastest hydrolysis reaction.
HO
FOR
A
Alcohol I, pKa =16.0
B
Alcohol II, pKa =10.0
C
Alcohol III, pKa = 7.2
+ ROH
D
Alcohol IV, pKa = 6.6
Curved arrows are used to illustrate the flow of electrons. Using
the provided starting and product structures, draw the curved
electron-pushing arrows for the following reaction or
mechanistic step(s).
Be sure to account for all bond-breaking and bond-making
steps.
:0:
NaOH, H₂O
00:4
Na O
heat
NaO
Select to Add Arrows
Select to Add Arrows
:0:
Na
a
NaOH, H2O
:0:
NaOH,
H2O
heat
heat
Na
ONH
Select to Add Arrows
Curved arrows are used to illustrate the flow of electrons. Using
the provided starting and product structures, draw the curved
electron-pushing arrows for the following reaction or
mechanistic step(s).
Be sure to account for all bond-breaking and bond-making
steps.
H
CH3NH3+
:0:
:0:
HO
CH3NH2
HH
iSelect to Add Arrows i
Select to Add Arrows i
HH
CH3NH3+
CH3NH2
Select to Add Arrows i
CH3NH3
CH3NH2
ايكدا
HH
Select to Add Arrows
Chapter 14 Solutions
Organic Chemistry - Standalone book
Ch. 14.3 - Prob. 1PCh. 14.3 - Prob. 2PCh. 14.4 - The 1H NMR signal for bromoform (CHBr3) appears at...Ch. 14.5 - identify the most shielded and least shielded...Ch. 14.5 - (a) Assign the chemical shifts 1.6, 2.2, and 4.8...Ch. 14.5 - Assign the chemical shifts 1.1, 1.7, 2.0, and 2.3...Ch. 14.5 - Assign the chemical shifts 1.6, 4.0, 7.5, 8.2, and...Ch. 14.6 - The 300-MHz 1H NMR spectrum of 1,4-dimethylbenzene...Ch. 14.6 - Prob. 9PCh. 14.6 - How many signals would you expect to find in the...
Ch. 14.7 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.8 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.11 - Prob. 13PCh. 14.11 - Prob. 14PCh. 14.12 - Hydrogen bonding between the oxygen of dimethyl...Ch. 14.14 - Prob. 16PCh. 14.15 - The 13C NMR spectrum of 1-bromo-3-chloropropane...Ch. 14.15 - Consider carbons x, y, and z in p-methylanisole....Ch. 14.15 - Prob. 19PCh. 14.16 - To which of the compounds of Problem 14.16 does...Ch. 14.18 - DEPT spectra for a compound with the formula...Ch. 14.20 - Vibrational frequencies are sensitive to isotopic...Ch. 14.21 - Prob. 23PCh. 14.22 - Prob. 24PCh. 14.23 - Prob. 25PCh. 14.23 - Which one of the C5H8 isomers shown has its max at...Ch. 14.24 - Knowing what to look for with respect to isotopic...Ch. 14.24 - The base peak appears at m/z105 for one of the...Ch. 14.24 - Mass spectra of 1-bromo-4-propylbenzene and...Ch. 14.25 - Prob. 30PCh. 14 - Each of the following compounds is characterized...Ch. 14 - Deduce the structure of each of the following...Ch. 14 - From among the isomeric compounds of molecular...Ch. 14 - The H1NMR spectrum of fluorene has signals at 3.8...Ch. 14 - Prob. 35PCh. 14 - H1NMR spectra of four isomeric alcohols with...Ch. 14 - Prob. 37PCh. 14 - We noted in Section 14.13 that an NMR spectrum is...Ch. 14 - Identify each of the C4H10O isomers on the basis...Ch. 14 - A compound (C3H7ClO2) exhibited three peaks in its...Ch. 14 - Label nonequivalent carbons in the following...Ch. 14 - Compounds A and B are isomers of molecular formula...Ch. 14 - C13 NMR spectra for four isomeric alkyl bromides...Ch. 14 - Prob. 44PCh. 14 - Prob. 45PCh. 14 - Identify the C3H5Br isomers on the basis of the...Ch. 14 - Prob. 47PCh. 14 - A compound (C8H10O) has the IR and H1NMR spectra...Ch. 14 - Deduce the structure of a compound having the...Ch. 14 - Figure 14.53 presents IR, H1NMR, C13NMR and mass...Ch. 14 - H1NMR, C13NMR, IR, and mass spectra are shown for...Ch. 14 - 1H NMR and IR spectra for a compound with the...Ch. 14 - FriedelCraftsalkylation of benzene with...Ch. 14 - Prob. 54DSPCh. 14 - Prob. 55DSPCh. 14 - Prob. 56DSPCh. 14 - Prob. 57DSPCh. 14 - Prob. 58DSP
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