ORGANIC CHEMISTRY-MOLYMOD PACKAGE
5th Edition
ISBN: 9781260227307
Author: SMITH
Publisher: MCG
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Chapter 12, Problem 12.34P
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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draw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocation
Table 6.4. Oxidation: Reaction with Baeyer’s reagent (cold, dilute, neutral, aqueous KMnO4) Write (+) if the reaction is positive, (-) if negative.
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OBSERVATIONS
+/-
cyclohexane
cyclohexene
benzene
toluene
acetylene
Enumerate the classes of hydrocarbons that are oxidizable by Baeyer’s reagent.
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What is the structural feature of these classes of hydrocarbons?
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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?
Chapter 12 Solutions
ORGANIC CHEMISTRY-MOLYMOD PACKAGE
Ch. 12 - Prob. 12.1PCh. 12 - Problem 12.2 What alkane is formed when each...Ch. 12 - Prob. 12.3PCh. 12 - Prob. 12.4PCh. 12 - Prob. 12.5PCh. 12 - Prob. 12.6PCh. 12 - Compound Molecular formula before...Ch. 12 - Problem 12.8 Draw the products formed when...Ch. 12 - Prob. 12.9PCh. 12 - Prob. 12.10P
Ch. 12 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Problem 12.14 Draw the products of each...Ch. 12 - Prob. 12.15PCh. 12 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12 - Prob. 12.17PCh. 12 - Problem 12.18 Draw the products formed when both...Ch. 12 - Problem 12.19 Draw the products formed when each...Ch. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Problem 12.22 Draw the products formed when each...Ch. 12 - Prob. 12.23PCh. 12 - Problem 12.24 Draw the organic products in each of...Ch. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Problem 12.27 Draw the products of each Sharpless...Ch. 12 - Prob. 12.28PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 12.30PCh. 12 - 12.31 Devise a synthesis of the following compound...Ch. 12 - Prob. 12.32PCh. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - 12.37 Stearidonic acid (C18H28O2) is an...Ch. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Draw the organic products formed in each reaction....Ch. 12 - Prob. 12.41PCh. 12 - Prob. 12.42PCh. 12 - Prob. 12.43PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - Prob. 12.45PCh. 12 - 12.46 (a)What product is formed in Step [1] of the...Ch. 12 - Draw the products formed after Steps 1 and 2 in...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. 12.50PCh. 12 - Prob. 12.51PCh. 12 - Prob. 12.52PCh. 12 - Prob. 12.53PCh. 12 - 12.54 An unknown compound A of molecular formula ...Ch. 12 - 12.55 DHA is a fatty acid derived from fish oil...Ch. 12 - Prob. 12.56PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.58 Epoxidation of the following allylic alcohol...Ch. 12 - Prob. 12.59PCh. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 12.61PCh. 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. 12.64PCh. 12 - Prob. 12.65PCh. 12 - 12.66 Devise a synthesis of each compound from the...Ch. 12 - Prob. 12.67PCh. 12 - Prob. 12.68PCh. 12 - 12.69 Devise a synthesis of each compound from as...Ch. 12 - Prob. 12.70PCh. 12 - Prob. 12.71PCh. 12 - 12.72 Draw a stepwise mechanism for the following...Ch. 12 - Prob. 12.73PCh. 12 - Prob. 12.74PCh. 12 - 12.75 Sharpless epoxidation of allylic alcohol X...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- For each alkane, which mono brominated derivatives could you form in good yield by free-radical bromination?(a) cyclopentane (b) methylcyclopentane(c) 2-methylpentane (d) 2,2,3,3-tetramethylbutanearrow_forwardWhat synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration reaction sequence? anti-Markovnikov addition of H 2O, preventing skeletal rearrangement anti-Markovnikov addition of H2O, promoting skeletal rearrangement Markovnikov addition of H 2O, preventing skeletal rearrangement Markovnikov addition of H 2O, promoting skeletal rearrangement anti-Markovnikov addition of H2O, syn-hydroxylationarrow_forwardTRUE OR FALSE I. The reaction of BH3 with 2-methylbut-2-ene results in the attachment of a hydroxyl group, OH, on the third carbon since this carbon is less substituted. II. The reduction of an alkyne using a strong base such as LiNH2 gives an alkane when 2 equivalents of hydrogen gas is added. III. Hydrobromination of an alkene follows anti-Markovnikov’s rule in the presence of a peroxide.arrow_forward
- complete the conversion using SN1, SN2, E1, or E2. what is a possible reagent? cyclohexane --> cyclodi-1, 3- enearrow_forwardThe heat of hydrogenation of cis-2,2,5,5-tetramethyl-3-hexene is -154 kJ (-36.7 kcal)/ mol, while that of the trans isomer is only -113 kJ (-26.9 kcal)/mol. Q.) Why is the heat of hydrogenation of the cis isomer so much larger (more negative) than that of the trans isomer?arrow_forwardAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forward
- Look at Figure 4-12 on page 105, and estimate the percentages of axial and equatorial conformations present at equilibrium in bromocyclohexane.arrow_forwardGiven the table , please calculate the theoretical and percentage yield of the starting material(cyclohexanol and sulfuric acid) and product(cyclohexene). densities: cyclohexanol-0.948 sulfuric acid-1.84 cyclohexene- 0.811arrow_forwardHow do you convert 1-butene to 2-bromobutane and 1,2-dibromobutane?arrow_forward
- Zaitsev’s rule: states " The alkene formed in greatest amount is the one that corresponds to A. removal of the hydrogen from the alpha-carbon having the fewest hydrogen substituents B. removal of the hydrogen from the any-carbon having the fewest hydrogen substituents C. removal of the water molecule from the alpha-carbon having the fewest hydrogen substituents D. removal of the hydroxyl (OH) from the any carbon having the fewest hydrogen substituents E. addition of hydrogen to more substituted carbon atomarrow_forwardPredict the energy difference between pent-1-ene and cis-pent-2-ene.arrow_forwardWhich is the most stable: 3,4-dimethyl-2-hexene, 2,3-dimethyl-2-hexene, or 4,5-dimethyl-2-hexene? a. Which compound has the largest heat of hydrogenation? b. Which compound has the smallest heat of hydrogenation?arrow_forward
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