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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Dehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.
Predict the energy difference between pent-1-ene and cis-pent-2-ene.
1. Consider the following reaction - Dehydrogenation of Methyl Cyclohexane (MCH) to Toluene
(TOL) using a Precious Metal (Pt) supported on Alumina.
CH3
CH3
2
()
+ 3 H₂
Typically, hydrogenation of a cyclo-alkane, like MCH, occurs in 3 or more stages, where one
bond is dehydrogenated per stage, eventually resulting in the dehydrogenation of 3 bonds.
Strong adsorption of MCH is likely to occur, but the adsorption of hydrogen (either as a
molecule on a single site OR as an atom on a single site) is unclear. Therefore, in this
question, two types of reaction mechanisms are to be considered, as discussed below:
(a) You are to first propose a reaction mechanism which includes adsorption, surface reaction,
and desorption. For each of the following cases, please write down a full set of elementary
reaction mechanisms.
(0)
Extraction of Hydrogen in 3 stages, based on dehydrogenation of each bond-where
the ensuing hydrogen product is adsorbed as a molecule on a single site, in one
step.…
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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- 3. 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_forwardDraw the alkene that would react with the reagent given to account for the product formed. ? + + H₂O **** H₂S04 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. CH3 CH3 CHCCH3 | | OH CH3 +1arrow_forward● Rank the following alkenes from most to least stable. A 11 B ||| MacBook Air C IVarrow_forward
- H,C. CH-CH,CH2-Br H3C NaNH, / NH3(1) CH;CH,-C=C-H • You do not have to consider stereochemistry. Separate multiple products using the + sign from the drop-down menu. • If no reaction occurs, draw the organic starting material.arrow_forward2) (4pts) Classify each reaction as addition, elimination, substitution, or rearrangement. A) CH;CH2B LIOH CH;CH2OH LiBr B) CH;CH2CH,Cl CH-CH-CH2 + + HCl C) CH;CH=CH2 H2 CH;CH2CH3 Verdana 10pt B IU A varrow_forwardDraw the alkene that would react with the reagent given to account for the product formed. CH3 HCI CH3 CHCCH, ? + Či CH3 You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forward
- The enthalpy for hydrogenation of different isomers of butene is shown in the following figure. Which statement below best interprets this figure? Hy I3D H2 7k mot 5kJ mot + H2 AH-120 kJ mot AH"-127 kJ mot AH-115 kJ mot © GMU 2020 Stability and hydrogenation enthalpies are not correlated. Butene II is less stable than butene I by 7 kJ/mol. O Butene Il is 7 kJ/mol more stable than I and 5 kJ/mol more stable than III. Butene II is 5 kJ/mol less atable than butene IlI. Enthalpyarrow_forwardWhich is not an alkene formed when 2-chloro-2-methylbutane is dehydrohalogenated with NaOCH2CH3 (sodium ethoxide)? O 2-methyl-but-2-ene O 1-methylcyclobut-1-ene 2-methyl-but-1-enearrow_forward4. A student was asked to prepare an alkene X in high yield using any alcohol as starting material CH3 CH,-C -CH=CH, CH3 X He chose 3, 3-dimethylbutan-2-ol (XI) and carried out a dehydration reaction. He was however horrified to note that the only alkene obtained was XII. CH3 OH CH3 CH;-C=C-CH3 conc. H,SO4 CH-CH3 heat CH3 CH3 XI XII i) Explain what went wrong here, and why X could not be formed from 3, 3-dimethylbutan-2-ol. Use structures to help support your answer. ii) Give an equation to show a much better method for preparing X in high yield. 5. Analyze the following structure and write one combination for Grignard reagent and a carbonyl that would give rise to it. CH,-CH,-OHarrow_forward
- Intermidiates and reagents of the following two final products from a Acetylene Note: the final products are different reactions but use the same starting material.arrow_forward3Which of the following alkyl radicals is the most stable? O A. CH3 O B. CH2. CH3 OD. CH3 O E. CH3 CH3CCH,CH3 CH;CHCH,CH3 · CH2CHCH;CH3 CH;CHCHCH3 CH;CHCH,CH2arrow_forwardThe two alkenes below react with HI at different rates. CH3CH=CHCH3 and CH₂=CH₂ Draw the structural formula of the MAJOR product formed by the alkene having the HIGHER reaction rate. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. TAYY [ ] در ChemDoodle Ⓡarrow_forward
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