EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393630817
Author: KARTY
Publisher: W.W.NORTON+CO. (CC)
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Chapter 17, Problem 17.37P
Interpretation Introduction
Interpretation:
The detailed mechanism for the given reaction is to be provided.
Concept introduction:
Strong nucleophiles are added across the carbonyl compounds having polar pi bonds. A nucleophile tends to form a bond with the atom at the positive end of a polar pi bond.
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1,4-Dimethyl-1,3-cyclohexadiene can undergo 1,2- or 1,4-addition with hydrogen halides. (a) 1,2-Addition i. Draw the carbocation intermediate(s) formed during the 1,2-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,2-addition product formed during the reaction in (i)? (b) 1,4-Addition i. Draw the carbocation intermediate(s) formed during the 1,4-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,4-addition product formed from the reaction in (i)? (c) What is the kinetic product from the reaction of one mole of hydrobromic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (d) What is the thermodynamic product from the reaction of one mole of hydrobro-mic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (e) What major product will result when 1,4-dimethyl-1,3-cyclohexadiene is treated with one mole of hydrobromic acid at - 78 deg * C ? Explain your reasoning.
Give the product of the bimolecular elimination from each of the isomeric halogenated compounds.
Reaction A
Reaction B.
КОВ
CH₂
HotBu
+B+
ко
HOIBU
+Br+
Templates More
QQQ
Select Cv Templates More
Cras
QQQ
One of these compounds undergoes elimination 50x faster than the other. Which one and why?
Reaction A because the conformation needed for elimination places the phenyl groups and to each other
Reaction A because the conformation needed for elimination places the phenyl groups gauche to each other.
◇ Reaction B because the conformation needed for elimination places the phenyl groups gach to each other.
Reaction B because the conformation needed for elimination places the phenyl groups anti to each other.
Five isomeric alkenes. A through each undergo catalytic hydrogenation to give 2-methylpentane
The IR spectra of these five alkenes have the key absorptions (in cm
Compound
Compound A
–912. (§), 994 (5), 1643 (%), 3077 (1)
Compound B 833 (3), 1667 (W), 3050 (weak shoulder on C-Habsorption)
Compound C
Compound D)
–714 (5), 1665 (w), 3010 (m)
885 (3), 1650 (m), 3086 (m)
967 (5), no aharption 1600 to 1700, 3040 (m)
Compound K
Match each compound to the data presented.
Compound A
Compound B
Compound C
Compound D
Compound
Chapter 17 Solutions
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
Ch. 17 - Prob. 17.1PCh. 17 - Prob. 17.2PCh. 17 - Prob. 17.3PCh. 17 - Prob. 17.4PCh. 17 - Prob. 17.5PCh. 17 - Prob. 17.6PCh. 17 - Prob. 17.7PCh. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Prob. 17.14PCh. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22PCh. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - Prob. 17.27PCh. 17 - Prob. 17.28PCh. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - Prob. 17.33PCh. 17 - Prob. 17.34PCh. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - Prob. 17.38PCh. 17 - Prob. 17.39PCh. 17 - Prob. 17.40PCh. 17 - Prob. 17.41PCh. 17 - Prob. 17.42PCh. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Prob. 17.46PCh. 17 - Prob. 17.47PCh. 17 - Prob. 17.48PCh. 17 - Prob. 17.49PCh. 17 - Prob. 17.50PCh. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - Prob. 17.53PCh. 17 - Prob. 17.54PCh. 17 - Prob. 17.55PCh. 17 - Prob. 17.56PCh. 17 - Prob. 17.57PCh. 17 - Prob. 17.58PCh. 17 - Prob. 17.59PCh. 17 - Prob. 17.60PCh. 17 - Prob. 17.61PCh. 17 - Prob. 17.62PCh. 17 - Prob. 17.63PCh. 17 - Prob. 17.64PCh. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - Prob. 17.68PCh. 17 - Prob. 17.69PCh. 17 - Prob. 17.70PCh. 17 - Prob. 17.71PCh. 17 - Prob. 17.72PCh. 17 - Prob. 17.73PCh. 17 - Prob. 17.74PCh. 17 - Prob. 17.75PCh. 17 - Prob. 17.76PCh. 17 - Prob. 17.77PCh. 17 - Prob. 17.78PCh. 17 - Prob. 17.79PCh. 17 - Prob. 17.80PCh. 17 - Prob. 17.81PCh. 17 - Prob. 17.82PCh. 17 - Prob. 17.83PCh. 17 - Prob. 17.84PCh. 17 - Prob. 17.1YTCh. 17 - Prob. 17.2YTCh. 17 - Prob. 17.3YTCh. 17 - Prob. 17.4YTCh. 17 - Prob. 17.5YTCh. 17 - Prob. 17.6YTCh. 17 - Prob. 17.7YTCh. 17 - Prob. 17.8YTCh. 17 - Prob. 17.9YTCh. 17 - Prob. 17.10YTCh. 17 - Prob. 17.11YTCh. 17 - Prob. 17.12YTCh. 17 - Prob. 17.13YTCh. 17 - Prob. 17.14YT
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