Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 13, Problem 5Q
Interpretation Introduction
Interpretation:
The given resonance structure thataccount for the lack of
Concept introduction:
In
In
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Compare with explanation the acidity of the following pairs of compounds.
(Note: You must draw the appropriate resonance structures to support your
answers.)
(c)
(i)
.COOH
.COOH
H3CO
Another reagent that can be used to convert carboxylic acids into acid chlorides is phosphorus
trichloride (PCI3), as shown in the scheme below.
:0:
:0:
:ö:
PCI2
+
-PCI2
H.
H
:O:
+ НОРCI2
The mechanism, for the reaction, is shown above but the curved arrows and the formal
charges, on the respective atoms, have been omitted.
(a) Draw the missing curved arrows for each step
(b) Supply any missing formal charges
Pick all of the symmetric resonance structures of the SO2 molecule.
(a) ö=s-ö:
(d) ö=s=Ö:
(9) : ö –s=ö
(b) : ö =s=ö
(e) Ö=s=ö
(h) ö-s-ö
(c) ö=s-Ö:
(1) :ö-s-0:
(1) :Ö-s=ö
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 1PPCh. 13 - Prob. 2PPCh. 13 - Prob. 3PPCh. 13 - Practice Problem 13.4 From each set of resonance...Ch. 13 - Practice Problem 13.5 The following enol (an...Ch. 13 - Prob. 6PPCh. 13 - Practice Problem 13.7
Two compounds, A and B, have...Ch. 13 - Prob. 8PPCh. 13 - Prob. 9PPCh. 13 - Prob. 10PP
Ch. 13 - Prob. 11PPCh. 13 - Prob. 12PPCh. 13 - Prob. 13PPCh. 13 - Prob. 14PPCh. 13 - Prob. 15PPCh. 13 - Practice Problem 13.16
Diels–Alder reactions also...Ch. 13 - Prob. 17PPCh. 13 - Prob. 18PCh. 13 - What product would you expect from the following...Ch. 13 - Prob. 20PCh. 13 - Prob. 21PCh. 13 - Provide the reagents necessary for each of the...Ch. 13 - Prob. 23PCh. 13 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - When 1-pentene reacts with N-bromosuccinimide...Ch. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - 13.31 Provide a mechanism that explains formation...Ch. 13 - 13.32 Provide a mechanism that explains formation...Ch. 13 - Treating either 1-chloro-3-methyl-2-butene or...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Although both 1-bromobutane and 4-bromo-1-butene...Ch. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Prob. 44PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 47PCh. 13 - Prob. 48PCh. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Explain the product distribution below based on...Ch. 13 - Mixing furan (Problem 13.44) with maleic anhydride...Ch. 13 - Prob. 53PCh. 13 - Prob. 54PCh. 13 - Prob. 1LGPCh. 13 - Prob. 2LGPCh. 13 - Prob. 1QCh. 13 - Prob. 2QCh. 13 - Prob. 3QCh. 13 - Prob. 4QCh. 13 - Prob. 5Q
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- The bond length of the indicated C-C single bond in hexa-1,3,5-triene is about 146 pm, which is considerably shorter than that in ethane, H3C-CH3. (a) How much shorter is it? Hint: See Figure 14-2, page 685. (b) Which occupied T MOS (obtained in Problem 14.32) help decrease this bond length? (c) If an electron were promoted from the HOMO to the LUMO, would the length of the C-C single bond increase, decrease, or stay roughly the same? Explain. 146 pmarrow_forwardThiocyanic acid (HSCN) is an inorganic acid (pKa = 1.1 at 25 °C) that can be classified as “strong” largely due to resonance stabilization of its conjugate base, thiocyanate (SCN– ). In the space provided below, draw Lewis electron dot structures of SCN- and all of its important resonance forms.arrow_forward6) (a) State with reasons whether the following compounds are aromatic, antiaromatic, or nonaromatic (1) HC=C=CH NH NH (iii) (iv) (b) Which is more stable, cyclobutadiene or 1,3-butadiene? Explain. ( (v)arrow_forward
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