Concept explainers
(a)
Interpretation: The important resonance hybrids for the given allylic carbocations have to be drawn and ranked based on their contributions.
Concept Introduction:
Allylic systems:
The allylic system is characterized by the connectivity of a single bonded carbon atom connected to double bond
Stability of the allylic carbocations:
Example for Primary allylic carbocation is:
Example for Secondary allylic carbocation is:
Example for tertiary allylic carbocation is:
(b)
Interpretation: The important resonance hybrids for the given allylic carbocations have to be drawn and ranked based on their contributions.
Concept Introduction:
Allylic systems:
The allylic system is characterized by the connectivity of a single bonded carbon atom connected to double bond alkene functional group as shown here:
Stability of the allylic carbocations:
Example for Primary allylic carbocation is:
Example for Secondary allylic carbocation is:
Example for tertiary allylic carbocation is:
(c)
Interpretation: The important resonance hybrids for the given allylic carbocations have to be drawn and ranked based on their contributions.
Concept Introduction:
Allylic systems:
The allylic system is characterized by the connectivity of a single bonded carbon atom connected to double bond alkene functional group as shown here:
Stability of the allylic carbocations:
Example for Primary allylic carbocation is:
Example for Secondary allylic carbocation is:
Example for tertiary allylic carbocation is:
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Chapter 20 Solutions
Organic Chemistry
- Compounds P and Q can undergo a Diels-Alder reaction to form two regioisomeric products R and S as shown in Figure 5. OMe O C8H12O2 R C8H12O2 S Figure 5 Draw the chemical structures of regioisomeric compounds R and S. Using possible resonance contributors of P and Q predict which of the two regioisomers will be favoured in the reaction. Using curly arrows, draw the mechanism for the reaction of P and Q to form the dominant regioisomer you have predicted in your answer to part (ii) above.arrow_forwarda) Draw the arrow-pushing mechanism for the reaction of hydronium with ethanol. Include all lone pairs and non-zero formal charges. b) Draw the arrow-pushing mechanism for the reaction of NaNH₂ with chloroform. Include all lone pairs and non-zero formal charges. c) Draw the arrow-pushing mechanism for the reaction of sodium hydroxide with phenol. Include all lone pairs and non-zero formal charges. d) Are any of the above reactions reversible? Do any of them go to completion? Explain your answer.arrow_forwardRank the alkenes shown in the ball-and-stick models (A–C) in order of increasing stability.arrow_forward
- The hydrobrominationof 2-methyl-1-butene could theoretically lead to 2 different alkyl bromides; in practice only one product is formed. Draw the structure of both theoretical products, circle the one that is actually produced, and briefly explain whyonly one product forms.arrow_forwardWhat are the following alkenes, E or Z? if neither label as such as with botharrow_forward1) Propose a synthesis of the following compound using ethanol as the only source of carbon atoms. 2) Rank the following from most stable to least stable.arrow_forward
- give answer in step by steparrow_forwardResveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.arrow_forwardDraw both resonance structures of the most stable carbocation intermediate in the reaction shown. Do not include the halide anion. Let Marvin JS adjust the number of hydrogens automatically as you use the charge tool to specify formal charge. + HCI Marvin JS - Troubleshooting Marvin JS - Compatibilityarrow_forward
- Define the below statement ? Benzene's six π electrons make it electron rich, so it reacts withelectrophiles.arrow_forwardConsider this scheme. Why does a ring form with a single ethylene glycol on A rather than two molecules of ethylene glycol to form acyclic acetals? Intramolecular reactions are A unfavorable when compared to intermolecular reactions Acyclic molecules are unfavorable compared to rings В in all cases The change in entropy is favorable for ring formation and strain is low in a five- membered ring Sterics prevents acyclic molecules from forming in this D case H HCI + HOCH2CH2OH H + H2Oarrow_forward(a) Rank the following carbocations in order of increasing electrophilicity (1 = lowest electrophilicity, 4 = highest electrophilicity). (b) Rank the following 1,1-halomethylcyclopentanes in order of reactivity in an SN1 reaction (1 = lowest reactivity, 4 = highest reactivity. CH3 CI B with SNI, nor reactive means more stable (c) Rank the following species in terms of increasing nucleophilicity in an SN2 reaction in a po aprotic solvent (1 = lowest nucleophilicity, 4 = highest nucleophilicity).arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning