(a)
Interpretation: All constitutional isomers formed in the given
Concept introduction: The removal of halide and neighboring
Answer to Problem 8.33P
All constitutional isomers formed in the given
Figure 1
Disubstituted alkene is the major product of the reaction.
Explanation of Solution
The
In the given compound, two
Figure 2
According to Zaitsev rule, more substituted alkene is obtained as a major product in
All constitutional isomers formed in the given
(b)
Interpretation: All constitutional isomers formed in the given
Concept introduction: The removal of halide and neighboring
Answer to Problem 8.33P
All constitutional isomers formed in the given
Figure 3
Monosubstituted alkene is the major product of the reaction.
Explanation of Solution
The
In the given compound, only one
Figure 4
According to Zaitsev rule, more substituted alkene is obtained as a major product in
All constitutional isomers formed in the given
(c)
Interpretation: All constitutional isomers formed in the given
Concept introduction: The removal of halide and neighboring
Answer to Problem 8.33P
All constitutional isomers formed in the given
Figure 5
Tetrasubstituted alkene is the major product of the reaction.
Explanation of Solution
The
In the given compound, three
Figure 6
According to Zaitsev rule, more substituted alkene is obtained as a major product in
All constitutional isomers formed in the given
(d)
Interpretation: All constitutional isomers formed in the given
Concept introduction: The removal of halide and neighboring
Answer to Problem 8.33P
All constitutional isomers formed in the given
Figure 7
Trisubstituted alkene is the major product of the reaction.
Explanation of Solution
The
In the given compound, two
Figure 8
According to Zaitsev rule, more substituted alkene is obtained as a major product in
All constitutional isomers formed in the given
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Chapter 8 Solutions
ORGANIC CHEMISTRY SOLUTIONS MANUAL
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- Draw a stepwise mechanism for the following reaction, which forms the four-membered ring in azelnidipine, a drug used as a calcium channel blocker sold in Japan.arrow_forwardOne step in the synthesis of the antihistamine fexofenadine involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.arrow_forwardProvide the missing starting material, reactant or product. Show appropriate stereochemistry. a) b)arrow_forward
- Draw a stepwise mechanism for the following Robinson annulation. This reaction was a key step in a synthesis of the steroid cortisone by R. B. Woodward and co-workers at Harvard University in 1951.arrow_forwardselect the expected major organic product.arrow_forwardDraw a stepwise mechanism for the attached reaction, which involves two Friedel–Crafts reactions. B was an intermediate in the synthesis of the antidepressant sertralinearrow_forward
- Draw a stepwise mechanism for the following reaction, a key step in the synthesis of the anti-inammatory drug celecoxib (trade name Celebrex).arrow_forwardDevise a stepwise synthesis of attached compound from dicyclopentadieneusing a Diels–Alder reaction as one step. You may also use organiccompounds having ≤ 4 C's, and any required organic or inorganicreagents.arrow_forward(−)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomer isolated from the tailflower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.arrow_forward
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