Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 8, Problem 8.19P
Interpretation Introduction
Interpretation:
The fraction of each monofluoro product formed in the fluorination of 2-methylbutane has to be estimated.
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2. In the bromination reactions, what is the function of CCl4? Why can it fulfil its role?3. Bromination proceeds by either free radical substitution or electrophillic addition. Based on Table 3, which mechanism is followed by alkanes? by alkenes? by alkynes?4. For which hydrocarbon type is light necessary for bromination to take place?5. What is the function of light in the bromination reaction? Why are alkenes and alkynes not included as samples?
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 atom
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-tetramethylbutane
Chapter 8 Solutions
Organic Chemistry
Ch. 8.2 - Prob. 8.1PCh. 8.4 - Name and draw structural formulas for all...Ch. 8.4 - Using the table of bond dissociation enthalpies in...Ch. 8.5 - Prob. 8.4PCh. 8.6 - Given the solution to Example 8.5, predict the...Ch. 8.7 - Prob. 8.6PCh. 8.7 - Linoleic acid is shown below. What makes this...Ch. 8.7 - Prob. BQCh. 8.7 - Prob. CQCh. 8.7 - The strength of the HO bond in vitamin E is weaker...
Ch. 8.7 - Prob. EQCh. 8.8 - Prob. 8.7PCh. 8 - Prob. 8.8PCh. 8 - Prob. 8.9PCh. 8 - Prob. 8.10PCh. 8 - Prob. 8.11PCh. 8 - Account for the fact that among the chlorinated...Ch. 8 - Name and draw structural formulas for all possible...Ch. 8 - Prob. 8.14PCh. 8 - There are three constitutional isomers with the...Ch. 8 - Following is a balanced equation for bromination...Ch. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Prob. 8.19PCh. 8 - Cyclobutane reacts with bromine to give...Ch. 8 - Prob. 8.21PCh. 8 - Following is a balanced equation for the allylic...Ch. 8 - Prob. 8.23PCh. 8 - Prob. 8.24PCh. 8 - The major product formed when methylenecyclohexane...Ch. 8 - Prob. 8.26PCh. 8 - Prob. 8.27PCh. 8 - Prob. 8.28PCh. 8 - Write the products of the following sequences of...Ch. 8 - Using your reaction roadmap as a guide, show...Ch. 8 - Prob. 8.31PCh. 8 - Prob. 8.32PCh. 8 - Prob. 8.33PCh. 8 - Prob. 8.34P
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- Explain why heats of hydrogenation cannot be used to determine the relative stability of 2-methylpent-2-ene and 3-methylpent-1-ene. A, B, and C, each subjected to hydrogenation. The number of rings and π bonds refers to the reactant (A, B, or C) prior to hydrogenation.arrow_forwardMarkovnikov's rule can best be explained by considering * a) the number of hydrogen atoms attached to each of the double bond carbons atoms. b) the number of alkyl groups attached to each of the double bond carbons atoms. c) the relative stabilities of the carbocations that can be formed from the alkene. d) the spatial arrangement of the groups around the double bond. e) All of the above are good explanations for Markovnikov's rule.arrow_forward2. In the bromination reactions, what is the function of CCl4? Why can it fulfil its role?3. Bromination proceeds by either free radical substitution or electrophillic addition. Based on Table 3, which mechanism is followed by alkanes? by alkenes? by alkynes?4. For which hydrocarbon type is light necessary for bromination to take place?arrow_forward
- Based on the hydrogenation and the bromination reaction information, how many different alkene structures can you draw that could be Compound X? (If enantiomers are possible, count each pair of enantiomers as one structure.)arrow_forwardWhich of the statement is INCORRECT? a. The increase in stability of 2,4-hexadiene over 1,3-hexadiene is due to the increased double bond substitution of the former. b. The stabilization of dienes by conjugation is less pronounced than the aromatic stabilization of benzene. c. Resonance description in alkenes usually involves charge separation. d. Higher energy pi-orbitals often have decreasing number of nodes.arrow_forwardFree-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield. What ratio of reactants (cyclohexane and chlorine) would you use for the synthesis of chlorocyclohexane?arrow_forward
- You have been tasked with the job of converting cyclohexane to iodocyclohexane. Radical iodination is not a feasible process (it is not thermodynamically favorable), so you cannot directly iodinate the starting cycloalkane that way. Propose an alternative strategy for performing the transformation of cyclohexane to iodocyclohexane. [Hint: you might not be able to do it in one step]arrow_forwardBromine adds to cis- and trans-2-butene to give different diastereomers of 2,3-dibromobutane. What does this say about the mode of addition of bromine to thisalkene?arrow_forwardExplain the General Features of Radical Reactions ?arrow_forward
- A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.arrow_forwardshow the similarities and differences in the chemical reactions between alkanes and alkenes in terms of bonding and mechanism for the following reactions: Combustion reaction (with oxygen) Homolytic substitution (Free radical substitution) (with at least Chlorine) Electrophilic addition (with at least bromine) You should use ethane and ethene to represent alkanes and alkenes, respectively.arrow_forwardAll 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) Complete hydrogenation of 2-Methylhexa-1,5-diene (b) Complete halogenation (Br2) of 3-Ethyl-2,2-dimethylhept-3-ene(c) Reaction of (4E)-2,4-Dimethylhexa-1,4-diene with a mole of waterarrow_forward
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