Both bicyclo[3.3.1]nonane and bicyclo[2.2.1]heptane are saturated hydrocarbons composed of only 2° and 3° carbons.Recall that radical substitution generally takes place preferentially at a 3° carbon. Indeed, when bicyclo[3.3.1]nonane istreated with bromotrichloromethane under irradiation, substitution takes place 100% at the 3° carbon. Under the sameconditions, however, no substitution is observed at the 3° carbon in bicyclo[2.2.1]heptane. Explain. Hint: Build molecularmodels of each of these compounds.BrCCl.hvhvBrBrBicyclo[3.3.1]nonane100%Bicyclo[2.2.1]heptane0%

Elimination reaction-is type of organic reaction in which two substituents are removed from molecule…

Answered: Both bicyclo[3.3.1]nonane and…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.44P

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Alkyl halides 1-chlorobutane 2-chlorobutane Allyl chloride 2-chloro-2-methylpropane 1-chloro-2-methylpropane 2-bromobutane SN2 conditions = Sodium Iodide in Acetone 1.Rank the alkyl halides according to their SN2 reactivity. If compounds are similar in reactivity, you may group them in your ranking. Considering substitution, leaving group, temperature, solvent, etc... provide an explanation for each pairwise ranking.
Kepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered-ring compounds. Show how these three pesticides are composed of two five-membered rings.
In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1-phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates—the product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon.
In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1- phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Whichproduct predominates—the product of inversion or the product of retention of conguration? (c) Suggest an explanation for this phenomenon.
Explain the substituent effect on properties of selected molecules such as resonance stability, acidity, acidic properties, basic properties and carbocation stability
For each of the following, write the major product(s) and then draw out each step in the mechanism using curved arrows. Show ALL lone pair electrons and formal charges. Redraw ALL molecules as to show explicitly ALL bonds being broken or formed. Identify the molecular orbital (HOMO) of the nucleophile and the molecular orbital (LUMO) of electrophile involved in the nucleophilic attack. MO diagrams are not necessary..
Estimate the stabilization gained as a result of conjugation when 1,4-pentadiene is converted to trans-1,3-pentadiene. Note that the answer is not as simple as comparing the heats of hydrogenation of 1,4-pentadiene and trans-1,3pentadiene. Although the double bonds are moved from unconjugated to conjugated, the degree of substitution of one of the double bonds is also changed, in this case, from a monosubstituted double bond to a trans disubstituted double bond. To answer this question, you must separate the effect that is the result of conjugation from that caused by a change in the degree of substitution.
Although the Dielsâ€“Alder reaction generally occurs between an electronrich diene and an electron-deficient dienophile, it is also possible to have inverse-demand Dielsâ€“Alder reactions between suitable electrondeficient conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Dielsâ€“Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regioisomer is possible, draw both.
Alcohols 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.
Alkyl halides 1-chlorobutane 2-chlorobutane Allyl chloride 2-chloro-2-methylpropane 1-chloro-2-methylpropane 2-bromobutane SN1 conditions = Silver Nitrate in Ethanol 1. Rank the alkyl halides according to their SN1 reactivity. If compounds are similar in reactivity, you may group them in your ranking. Considering substitution, leaving group, temperature, solvent, etc... provide an explanation for each pairwise ranking.
Provide a synthesis starting from benzene, toluene, bromocyclohexane and any other carbon compound having 4 carbons or less. Reagents not bonded in the final compound do not count for the 4-carbon rule, but you can use compounds like TsCl or PPh3.
A novel heterocyclic compound, M, contains nitrogen and sulfur atoms and exhibits interesting photochemical properties. When exposed to ultraviolet (UV) light at a specific wavelength, M undergoes a photoreaction resulting in two products: N and O. Product N is formed through a [2+2] cycloaddition involving the nitrogen atom in M, while product O results from a homolytic cleavage of a sulfur-sulfur bond in M. Given these reaction pathways, what is the most probable structure of M, and what are the likely structures of N and O? A. M is a thiazole derivative; N is a dimerized product through the nitrogen atoms, and O is a compound with two sulfur-centered radicals. B. M is a diazine derivative; N is a tetra-atomic cyclic compound, and O is a compound with two separate thiol groups. C. M is a thiadiazole derivative; N is a four-membered ring involving the nitrogen atom, and O results in two sulfur-centered radicals. D. M is a dithiolane derivative; N is a dimer involving the nitrogen…

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