
Concept explainers
(a)
Interpretation:
The detailed mechanisms for the given reaction occurring via
Concept introduction:
The
In case of

Answer to Problem 8.44P
The
The
Explanation of Solution
The given reaction equation is:
In the given reaction,
The hydrogen atom, indicated with the dash bond, is anti to
If the hydrogen atom, indicated with wedge bond, tends to eliminate, it must orient anti to
In
The products formed for the given reaction from both
(b)
Interpretation:
The detailed mechanisms for the given reaction occurring via
Concept introduction:
The
In case of

Answer to Problem 8.44P
The
The
Explanation of Solution
The given reaction equation is:
In the given reaction,
In
The products formed for the given reaction from both
(c)
Interpretation:
The detailed mechanisms for the given reaction occurring via
Concept introduction:
The
In case of

Answer to Problem 8.44P
The
The
Explanation of Solution
The given reaction equation is:
In the given reaction,
In
In the second step, the base abstracts the proton from the carbon adjacent to the positively charged carbon. Two products are possible because the proton gets eliminated from two different carbon atoms. The detailed mechanism is shown below:
The products formed for the given reaction from both
(d)
Interpretation:
The detailed mechanisms for the given reaction occurring via
Concept introduction:
The
In case of

Answer to Problem 8.44P
The
The
Explanation of Solution
The given reaction equation is:
In the given reaction,
In
In the second step, the base abstracts the proton from the carbon adjacent to the positively charged carbon. Two products are possible from the secondary carbocation because the proton is eliminated from two different carbon atoms.
The carbocation formed is a secondary carbocation, which can be rearranged to a more stable tertiary carbocation by
Two products are possible from the tertiary carbocation because the proton is eliminated from two different carbon atoms.
Thus, in all the reactions above, the products are formed by
The products formed for the given reaction from both
(e)
Interpretation:
The detailed mechanisms for the given reaction occurring via
Concept introduction:
The
In case of

Answer to Problem 8.44P
The
The
Explanation of Solution
The given reaction equation is:
In the given reaction,
In
In the second step, the base abstracts the proton from the carbon adjacent to the positively charged carbon. Two products are possible because the proton is eliminated from two different carbon atoms. The detailed mechanism is shown below:
The products formed for the given reaction from both
(f)
Interpretation:
The detailed mechanisms for the given reaction occurring via
Concept introduction:
The
In case of

Answer to Problem 8.44P
The
The
Explanation of Solution
The given reaction equation is:
In the given reaction,
In
In the second step, the base abstracts the proton from the carbon adjacent to positively charged carbon. Two products are possible because the proton is eliminated from two different carbon atoms. The detailed mechanism is shown below:
The carbocation formed is a secondary carbocation, which can be rearranged to form more stable tertiary carbocation by
Two products are possible from the tertiary carbocation because the proton IS eliminated from two different carbon atoms.
The products formed for the given reaction from both
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Chapter 8 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Synthesize 2-Ethyl-3-methyloxirane from dimethyl(propyl)sulfonium iodide using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forwardSynthesize 2-Hydroxy-2-phenylacetonitrile from phenylmethanol using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forwardSynthesize N-Methylcyclohexylamine from cyclohexanol using the necessary organic or inorganic reagents. Draw the structures of the compounds.arrow_forward
- 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 Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
