EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Question
Chapter 15, Problem 15.44AP
Interpretation Introduction
Interpretation:
The six-carbon conjugated diene that gives the same product on addition reaction either from
Concept introduction:
Conjugated dienes are defined as two double bonds separated by one single bond. They are more stable than non-conjugated double bonds due to resonance and hybridization energy. Along with that the heat of hydrogenation effects the stability of conjugated dienes. It states that higher the heat of hydrogenation energy lowers the stability of dienes.
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Diels–Alder reaction of a monosubstituted diene (such as CH2=CH– CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant, and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.
Diels—Alder reaction of a monosubstituted diene (such as CH2 = CH – CH = CHOCH3) with a monosubstituted dienophile (such as CH2 = CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.
Diels–Alder reaction of a monosubstituted diene (such as CH2=CH–CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO)gives a mixture of products, but the 1,2-disubstituted product oftenpredominates. Draw the resonance hybrid for each reactant, and use thecharge distribution of the hybrids to explain why the 1,2-disubstitutedproduct is the major product.
Chapter 15 Solutions
EBK ORGANIC CHEMISTRY
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42APCh. 15 - Prob. 15.43APCh. 15 - Prob. 15.44APCh. 15 - Prob. 15.45APCh. 15 - Prob. 15.46APCh. 15 - Prob. 15.47APCh. 15 - Prob. 15.48APCh. 15 - Prob. 15.49APCh. 15 - Prob. 15.50APCh. 15 - Prob. 15.51APCh. 15 - Prob. 15.52APCh. 15 - Prob. 15.53APCh. 15 - Prob. 15.54APCh. 15 - Prob. 15.55APCh. 15 - Prob. 15.56APCh. 15 - Prob. 15.57APCh. 15 - Prob. 15.58APCh. 15 - Prob. 15.59APCh. 15 - Prob. 15.60APCh. 15 - Prob. 15.61APCh. 15 - Prob. 15.62APCh. 15 - Prob. 15.63APCh. 15 - Prob. 15.64APCh. 15 - Prob. 15.65APCh. 15 - Prob. 15.66APCh. 15 - Prob. 15.67APCh. 15 - Prob. 15.68APCh. 15 - Prob. 15.69APCh. 15 - Prob. 15.70APCh. 15 - Prob. 15.71APCh. 15 - Prob. 15.72APCh. 15 - Prob. 15.73APCh. 15 - Prob. 15.74APCh. 15 - Prob. 15.75APCh. 15 - Prob. 15.76APCh. 15 - Prob. 15.77APCh. 15 - Prob. 15.78APCh. 15 - Prob. 15.79APCh. 15 - Prob. 15.80APCh. 15 - Prob. 15.81APCh. 15 - Prob. 15.82APCh. 15 - Prob. 15.83APCh. 15 - Prob. 15.84APCh. 15 - Prob. 15.85APCh. 15 - Prob. 15.86AP
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- In 4+2 cycloaddition, ENDO stereochemistry is preferred because: endo stereochemistry allows the diene to adopt s-cis conformation. endo stereochemistry results in less steric hindrance. the transition state leading to endo stereochemistry is higher energy. it allows for additional π to π overlap between the diene and the dienophile.arrow_forward4. Give the structure of a conjugated diene with the molecular formula of C7H12.arrow_forwardAddition of HBr to allene (CH2 = C = CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.arrow_forward
- Addition of HBr to allene (CH2=C=CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.arrow_forwardWhich isomer of 1-bromo-3-isopropylcyclohexane reacts faster when refluxed with potassium tert-butoxide, the cis isomer or the trans isomer? Draw the structure of the expected product from the faster-reacting compound.arrow_forwardRank the following dienes in their rate of reaction with the same dienophile in a Diels-Alder reaction. For example, 1 = fastest or most reactive diene, 4 = slowest or least reactive diene.arrow_forward
- Which diene is more reactive in a Diels–Alder reaction? CH2=CHCH=CHOCH3 or CH2=CHCH=CHCH2OCH3arrow_forwardDraw all possible stereoisomers of hepta-2,4-diene and label each double bond as E or Z.arrow_forwardHow many linear dienes have molecular formula C6H10? (Disregard cis–trans isomers.) A. How many of the linear dienes in part a are conjugated dienes? B. How many are isolated dienes? C. How many are cumulated dienes?arrow_forward
- Draw the reactants that would be used to form this cyclohexene derivative in a Diels- Alder reaction. Include any relevant stereochemical configurations. Draw Diene + ·00 aarrow_forwardName the 2 nonconjugated dienes with formula C6H₁0 that contain an unbranched chain. If there is only one diene, leave the second space blank. Do not use E/Z designators to indicate stereochemistry. Diene #1: Diene #2:arrow_forwardWhen HBr adds to a conjugated diene, what is the product-determining step?arrow_forward
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