Concept explainers
(a)
Interpretation: The reason as to why electrophilic substitution occurs on the ring without
Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.
(b)
Interpretation: The reason as to why electrophilic substitution occurs more readily at
Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.
(c)
Interpretation: The reason as to why electrophilic substitution occurs more readily at
Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.
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Organic Chemistry
- Which of the following are achiral? And identify the relationship between each of them. Ex. A-B, B-Darrow_forwardDrawing an SN2 product with More Complex Reactants Identify C, the product of an SN2 reaction in the synthesis of raloxifene, a drug used to reduce the risk of invasive breast cancer in postmenopausal women.arrow_forwardA. Arrange the following radicals in order of decreasing rate of bromination. Justify your answer. B. Trehalose and isomaltose are both dimers of glucose. However, they have considerablydifferent reactivities. Concisely explain why these differences are observed. -Isomaltose is a reducing sugar while trehalose is not.-Trehalose is very resistant to acid hydrolysis while isomaltose can be acid-hydrolyzed withease.arrow_forward
- Consider compound I below, which is structurally related to a natural product that was isolated from an extract of a Caribbean marine sponge (See J. Chem. Soc. 1994, 116, 6015). Answer the following questions about this compound (please explain answers) How many double bonds with E stereochemistry are present? _________ How many double bonds with Z stereochemistry are present? _________arrow_forwardBromide Bhas normal activity (for a secondary bromide) towards SN1 substitution, but A has much higher reactivity and Chas much lower reactivity.arrow_forwardDraw the structures and specify the stereochemistry of compounds A-C.arrow_forward
- Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?arrow_forwardaddition of hbr to a double bond with an ether (-or) substituent occurs regiospecifically to give a product in which the Br OR are bonded to the same carbon. Draw the two possible carbocation intermediates in this electrophilic addition reaction,and explain using resonance why the observed product is formed.arrow_forwardThe spirocyclic pentadiene derivative F shown below is converted stereospecificallyinto compound G on heating. The transformation involves two consecutive pericyclicreactions of the same type, and proceeds via compound H which is not isolated. Identify the type of pericyclic reaction occurring, and determine the structure ofcompound H.arrow_forward
- Draw the product of this reaction and states its IUPAC name, and states what type of mechanism is occuring (eg. SN1, SN2, E1, E2, etc)?arrow_forwardAlthough two products (A and B) are possible when naphthalene undergoes electrophilic aromatic substitution, only A is formed. Draw resonance structures for the intermediate carbocation to explain why this is observed.arrow_forwardExplain why the C=C of an enol is more nucleophilic than the C=C of an alkene, despite the fact that the electronegative oxygen atom of the enol inductively withdraws electron density from the carbon–carbon double bond.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning