Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 12, Problem 32P
Interpretation Introduction
Interpretation: The given
Concept introduction: Hydrogenation reaction is exothermic in nature due to the fact that the bonds are stronger in product than in reactant. Heat of hydrogenation can be used as measure for relative stability of alkenes when they are reduced to same
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4. The enthalpies, AH°, for the hydrogenation of three alkenes are shown below:
Alkene A: -50 kcal/mole
Alkene B: -60 kcal/mole
Alkene C: -70 kcal/mole
Which alkene is the least stable and why?
4. A double bond in a six-membered ring is usually more stable in an endocyclic position than
in an exocyclic position. Hydrogenation data on two pairs of compounds follow. One pair
suggests that the energy difference between endocyclic and exocyclic double bonds is
about 9 kJ/mol. The other pair suggests an energy difference of about 5 kJ/mol. Which
number do you trust as being more representative of the actual energy difference? Explain
your answer.
endocyclic
exоcyclic
107
116
105
110
heats of hydrogenation (kJ/mol)
In the reaction given below, what type of reaction is used?
n-Pentane
→ Isopentane
нннн
H
ITH
Н—С—с—С—с —О —Н
Н—с—с— с-с—н
||| |
H
нн
H
Addition
Elimination
Substitution
Rearrangement
Chapter 12 Solutions
Organic Chemistry (6th Edition)
Ch. 12.1 - Prob. 1PCh. 12.3 - Problem 12.2 What alkane is formed when each...Ch. 12.3 - Prob. 3PCh. 12.3 - Prob. 4PCh. 12.3 - Prob. 5PCh. 12.3 - Prob. 6PCh. 12.3 - Compound Molecular formula before...Ch. 12.4 - Problem 12.8 Draw the products formed when...Ch. 12.5 - Prob. 9PCh. 12.5 - Prob. 10P
Ch. 12.5 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12.5 - Prob. 12PCh. 12.5 - Prob. 13PCh. 12.6 - Problem 12.14 Draw the products of each...Ch. 12.8 - Prob. 15PCh. 12.8 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12.9 - Prob. 17PCh. 12.9 - Problem 12.18 Draw the products formed when both...Ch. 12.10 - Problem 12.19 Draw the products formed when each...Ch. 12.10 - Prob. 20PCh. 12.10 - Prob. 21PCh. 12.11 - Problem 12.22 Draw the products formed when each...Ch. 12.11 - Prob. 23PCh. 12.12 - Problem 12.24 Draw the organic products in each of...Ch. 12.13 - Prob. 25PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Prob. 33PCh. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - 12.48 Draw the products formed in each oxidative...Ch. 12 - What alkene or alkyne yields each set of products...Ch. 12 - Prob. 47PCh. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - Prob. 50PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 58PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - 12.63 Devise a synthesis of each compound from...Ch. 12 - Prob. 61P
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- The reaction of 3-methylene-1-cyclohexene and HBr yields the four products shown in the attachment. Which two are formed at high temperatures and which two are formed at low temperatures? Why? Why is 1-bromo-3-methylenecyclohexane not formed?arrow_forwardWhat does Zaitsev's rule state? As the degree of substitution around the C=C of an alkene decreases, the stability of alkene increases. O None of the statements is correct. As the degree of substitution around the C=C of an alkene decreases, the stability of alkene decreases. O As the degree of substitution around the C=C of an alkene increases, the stability of alkene decreases.arrow_forwardRank the alkenes from most stable to least stable.arrow_forward
- Identify the major product of this reaction of an alkene. | ||| OH OH 1. Hg(OAc)2, H2O 2. NaBH4, NaOH || IV ㅊ OH OHarrow_forwardIf a catalyst could be found that would establish an equilibrium between 1,2-butadiene and 2-butyne, what would be the ratio of the more stable isomer to the less stable isomer at 25°C? CH,=C=CHCH, CH,C=CCH, AG° = -16.7 kJ (-4.0 kcal)/molarrow_forward∆H° values obtained for a series of similar reactions are one set of experimental data used to determine the relative stability of alkenes. Explain how the following data suggest that cis-but-2-ene is more stable than but-1-ene (Section 12.3A).arrow_forward
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