(a)
Interpretation: The triene that has largest heat of hydrogenation is to be predicted.
Concept introduction: Conjugated diene consists of two double bonds that are separated by a single bond, whereas isolated diene also consists of two double bond but they are separated by two or more carbon atoms.
The stability of conjugated diene is more than isolated diene. Due to which the heat of hydrogenation is smaller for conjugated diene, whereas heat of hydrogenation for isolated diene is larger.
(b)
Interpretation: The triene that has smallest heat of hydrogenation is to be predicted.
Concept introduction: Conjugated diene consists of two double bonds that are separated by a single bond, whereas isolated diene also consists of two double bond but they are separated by two or more carbon atoms.
The stability of conjugated diene is more than isolated diene. Due to which the heat of hydrogenation is smaller for conjugated diene, whereas heat of hydrogenation for isolated diene is larger.
(c)
Interpretation: The triene that absorbs the longest
Concept introduction: Conjugated diene consists of two double bonds that are separated by a single bond, whereas isolated diene also consists of two double bond but they are separated by two or more carbon atoms.
The energy difference between the ground and excited state decreases when number of conjugated bonds increases. Due to this absorption shifts to the longer wavelengths.
(d)
Interpretation: The triene that is most reactive in the Diels-Alder reaction is to be predicted.
Concept introduction: Conjugated diene consists of two double bonds that are separated by a single bond, whereas isolated diene also consists of two double bond but they are separated by two or more carbon atoms.
The stability of conjugated diene is more than isolated diene.
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Chapter 16 Solutions
ORGANIC CHEMISTRY
- The heat of combustion of decahydronaphthalene (C10H18) is -6286 kJ/mol. The heat of combustion of naphthalene 1C10H82 is -5157 kJ/mol. (In both cases CO2(g) and H2O(l) are the products). Calculate the heat of hydrogenation and the resonance energy of naphthalene.arrow_forwardBased on the given information, determine the products of the Diels-Alder reaction.arrow_forwardWhich alkyne has the smaller heat of hydrogenation, HC=CCH,CH,CH, or CH,C=CCH,CH,? Explain your choice.arrow_forward
- Is Buckminsterfullerene Aromatic?arrow_forward3. The heat of hydrogenation for allene, H½C = C= CH2, to yield propane is – 295 kJ/mol, and the heat of hydrogenation for a typical monosubstituted alkene such as propene is -126 kJ/mol. Is allene more stable or less stable than you might expect for a diene ? Explain.arrow_forward5) Which of the following compounds is aromatic? B C H Darrow_forward
- Propylene does not undergo free radical polymerization readily because there are two competing steps after initiation: propagation and hydrogen atom abstraction.(a) Using a generic radical R• as a reactant with propylene, draw the mechanism and products for the two competing steps.(b) Which step produces the more stable product?(c) How do your results explain propylene’s poor reactivity in free radical polymerization?arrow_forwardHow does ring strain relates to aromaticity?arrow_forward4arrow_forward
- All about Alkene, Alkyne and Alkyl halides(1) Write a complete chemical equation showing reactants, products, and catalysts needed (if any) for the following reaction and (2) Draw and name the organic compound found in every reaction. (A) Reaction of cis-3,3-Dimethyl-4-propylocta-1,5-diene with two mole of HBr(B) Reaction of trans-1-Bromo-3-chlorocyclopentane with potassium hydroxide(C) Formation of Gilman reagent using isopropyl bromidearrow_forwardWhen HBr adds to (CH3)2C = CH2 under radical conditions, two radicals are possible products in the first step of chain propagation. Draw the structure of both radicals and indicate which one is formed. Then draw the preferred product from HBr addition under radical conditions.arrow_forwardDraw the structure of (E)-1-bromo-2-methyl-2-butene.arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning