Concept explainers
Interpretation:
The facts that can be suggested about the mechanism of the reaction for the given result are to be predicted.
Concept introduction:
Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.
Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.
Nucleophilic substitution reaction is a reaction in which an electron-rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.
Aryl halides undergo nucleophilic substitution reaction in the presence of a strong nucleophile.
Nucleophilic substitution reactions of aryl halides proceed through the elimination addition mechanism and benzyne is formed as the intermediate.
Hydroxide ions are nucleophiles; they are negatively charged species.
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EBK ORGANIC CHEMISTRY
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- (a) Propose a mechanism for the conversion of cis-hex-3-ene to the epoxide (3,4-epoxyhexane)and the ring-opening reaction to give the glycol, hexane-3,4-diol. In your mechanism, payparticular attention to the stereochemistry of the intermediates and products.(b) Repeat part (a) for trans-hex-3-ene. Compare the products obtained from cis- andtrans-hex-3-ene. Is this reaction sequence stereospecific?arrow_forwardThe sex attractant of the housefly has the formula C23 H46. When treated with warm potassium permanganate, this phero- mone gives two products: CH3(CH2)12COOH and CH3(CH2)7COOH. Suggest a structure for this sex attractant. Explain which part of the structure is uncertain.arrow_forwardConsider the following structural formulas. OH H;C CH3 CH3 F G H (a) Which of the compounds F-l can easily be subjected to an elimination reaction? (b) Provide the reaction mechanism for all eliminations under (a).arrow_forward
- Draw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)arrow_forwardWhen tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether. (a) What happens to the reaction rate if the concentration of ethanol is doubled?arrow_forwardPropose suitable reagents to accomplish the following transformations.arrow_forward
- When ethyl bromide is added to potassium tert-butoxide, the product is ethyl tert-butyl ether. (a) What happens to the rate if the concentration of potassium tert-butoxide is tripled and the concentration of ethyl bromide is doubled?arrow_forward15.38 In research into the stereochemistry of nucleophilic reactions, the following reaction was observed. HO DO HO methanol H₂O, formic acid HO (CH₂),COH major stereoisomer formed Show, by drawing structural formulas for any intermediate compounds formed, how the starting material is converted to the product.arrow_forwardRank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forward