ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Chapter 13, Problem 54P
Interpretation Introduction
Interpretation:
The resonating structures and resonance hybrid for the carbocation that could result from the ionization of bromine from
Concept introduction:
Resonance means delocalization of electrons within a molecule. It is also known as mesomerism.
A molecule in which delocalization of electron takes place is shown by various contributing structures and these contributing structures are called resonating structures.
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1,3-pentadiene reacts with HBr. When the double bond at the 3-position reacts, the hydrogen attaches to the 4-carbon, thus forming an allylic carbocation with delocalized electrons. This carbocation has another resonance structure. Because there are equal amounts of diene and hydrogen bromide, in which molecule only one of the double bonds reacts.
Which of the following correctly describes this new resonance structure?
a) It has a double bond between carbons 3 and 4
b) It has a positive charge on carbon 2
c) It has a positive charge on carbon 4
d) It has a double bond between carbons 2 and 3
Propose a structure for an aromatic hydrocarbon, C3H10, that can form three C3H,Br products on substitution of a hydrogen on the aromatic
ring with bromine.
• You do not have to consider stereochemistry.
In cases where there is more than one answer, just give one.
• Ignore the ortho, para-directing effects of the alkyl groups in answering this question. Consider only the number of nonequivalent hydrogens
on the aromatic ring.
....
ChemDoodle
write both the thermodynamic & kinetic
products for the reaction of:
1,3-pentadiene with HBr
Chapter 13 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
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 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 46PCh. 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. 2LGP
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