(a)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a
Elimination reactions are the reaction in which
(a)

Answer to Problem 8.46SP
The structure of an intermediate is shown in Figure 1.
The major product of the given reaction is shown in Figure 2.
Explanation of Solution
When
Figure 1
The chloride ion acts as a nucleophile that attacks on the electrophilic tertiary carbocation and results in the formation of
The major product of the given reaction is,
Figure 2
(b)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(b)

Answer to Problem 8.46SP
The structure of an intermediate is shown in Figure 3.
The major product of the given reaction is shown in Figure 4.
Explanation of Solution
When
Figure 3
Bromide ion opens the bromonium ion intermediate at the more substituted carbon atom and forms
Figure 4
(c)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(c)

Answer to Problem 8.46SP
The structure of an intermediate is shown in Figure 5.
The major product of the given reaction is shown in Figure 6.
Explanation of Solution
When
Figure 5
When
Figure 6
(d)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(d)

Answer to Problem 8.46SP
The structure of an intermediate is shown in Figure 7.
The major product of the given reaction is shown in Figure 8.
Explanation of Solution
When
Figure 7
Now, the ozonide intermediate reacts with dimethyl sulfide and forms acetaldehyde and
Figure 8
(e)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(e)

Answer to Problem 8.46SP
The major product of the given reaction is shown in Figure 9.
Explanation of Solution
When alkene reacts with
Figure 9
(f)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(f)

Answer to Problem 8.46SP
The major product of the given reaction is shown in Figure 10.
Explanation of Solution
When alkene reacts with
Figure 10
(g)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(g)

Answer to Problem 8.46SP
The major product of the given reaction is shown in Figure 11.
Explanation of Solution
When an alkene reacts with peroxyacid, it forms an
The major product of the given reaction is,
Figure 11
(h)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(h)

Answer to Problem 8.46SP
The structure of an intermediate is shown in Figure 12.
The major product of the given reaction is shown in Figure 13.
Explanation of Solution
Alkene undergoes
The structure of an intermediate is given as,
Figure 12
Now, the cyclic osmate undergoes oxidation in the presence of
Figure 13
(i)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(i)

Answer to Problem 8.46SP
The major product of the given reaction is shown in Figure 14.
Explanation of Solution
The major product of the given reaction is,
Figure 14
(j)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(j)

Answer to Problem 8.46SP
The structure of an intermediate is shown in Figure 15.
The major product of the given reaction is shown in Figure 16.
Explanation of Solution
When an alkene reacts with peroxyacid, it forms an epoxide or oxirane. Here,
The structure of an intermediate is given as,
Figure 15
The oxirane is opened at more substituted carbon atom in the presence of an acid
The major product of the given reaction is,
Figure 16
(k)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(k)

Answer to Problem 8.46SP
The major product of the given reaction is shown in Figure 17.
Explanation of Solution
Alkene undergoes oxidative cleavage in the presence of hot concentrated
The major product of the given reaction is,
Figure 17
(l)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(l)

Answer to Problem 8.46SP
The major product of the given reaction is shown in Figure 18.
Explanation of Solution
Alkene undergoes ozonolysis to form carbonyl compounds. Here,
The major product of the given reaction is,
Figure 18
(m)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(m)

Answer to Problem 8.46SP
The major product of the given reaction is shown in Figure 19.
Explanation of Solution
In this reaction,
The major product of the given reaction is,
Figure 19
(n)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(n)

Answer to Problem 8.46SP
The structure of an intermediate and the major product of the given reaction are shown in Figure 20.
Explanation of Solution
This reaction is an acid catalyzed hydration of alkene and forms
The structure of an intermediate and the major product of the given reaction is,
Figure 20
(o)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(o)

Answer to Problem 8.46SP
The major product of the given reaction is shown in Figure 21.
Explanation of Solution
The given reaction is an olefin metathesis. The major product of the given reaction is,
Figure 21
(p)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(p)

Answer to Problem 8.46SP
The structure of an intermediate is shown in Figure 22.
The major product of the given reaction is shown in Figure 24.
Explanation of Solution
Alkene reacts with mercuric acetate and forms mercurinium ion intermediate.
The structure of an intermediate is given as,
Figure 22
Now, water molecule acts as a nucleophile that opens the mercurinium ion at the most substituted carbon atom.
Figure 23
Now, organomercurial alcohol undergoes demercuration in the presence of
Figure 24
(q)
Interpretation:
The major product of the given reaction and the structure of any intermediate are to be predicted.
Concept introduction:
Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reaction in which alkenes are prepared. In this two substituents are eliminated by either one step or two step mechanism.
(q)

Answer to Problem 8.46SP
The structure of an intermediate is shown in Figure 25.
The major product of the given reaction is shown in Figure 26.
Explanation of Solution
Alkene reacts with chlorine and forms chloronium ion intermediate.
The structure of an intermediate is given as,
Figure 25
Now, the water molecule acts as a nucleophile that opens the chloronium ion intermediate at more substituted carbon atom. The major product of the given reaction is,
Figure 26
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Chapter 8 Solutions
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
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- Synthesize N-Methylcyclohexylamine from cyclohexanol using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forwardIf possible, please provide the formula of the compound 3,3-dimethylbut-2-enal.arrow_forwardSynthesize 1,4-dibromobenzene from acetanilide (N-phenylacetamide) using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forward
- Indicate the products obtained by mixing (3-oxo-3-phenylpropyl)triphenylphosphonium bromide with sodium hydride.arrow_forwardWe mix N-ethyl-2-hexanamine with excess methyl iodide and followed by heating with aqueous Ag2O. Indicate the major products obtained.arrow_forwardIndicate the products obtained by mixing acetophenone with iodine and NaOH.arrow_forward
- Indicate the products obtained by mixing 2-Propanone and ethyllithium and performing a subsequent acid hydrolysis.arrow_forwardIndicate the products obtained if (E)-2-butenal and 3-oxo-butanenitrile are mixed with sodium ethoxide in ethanol.arrow_forwardQuestion 3 (4 points), Draw a full arrow-pushing mechanism for the following reaction Please draw all structures clearly. Note that this intramolecular cyclization is analogous to the mechanism for halohydrin formation. COH Br + HBr Brarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

