E. Rank the following molecules in decreasing activation (from most activated =1 to most deactivated =6) based on the substituents present on the benzene ring. Also indicate whether the substituents are ortho-para or meta directors. HO -NH₂ CI
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- Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. H3C HCI / H2O `NH2 reflux • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na", I, in your answer. • In cases where there is more than one answer, just draw one. opy aste Previous NextAcyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. H3C. ... NH2 HCI/H₂O reflux • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one. + 4 n [ ?I H Ph Br In an E2 elimination reaction, the leaving group and the hydrogen atom must be anti-coplanar for this concerted reaction to occur. ||| Identify which of the following structures has the hydrogen atom and the leaving group aligned anti-coplanar. CH3 Ph Ph H TI F H || OH H Ph H CH3 CH3 Br Ph Br A) I B) II C) III
- For the given molecule, highlight any nucleophilic sites in red and any electrophilic sites in blue. O: 439 0-HFor SN1 Explain the order in which 2o (secondary) alkyl halides reacted (fastest to slowest) and explain why. 2o (secondary) compounds listed are: (see picture) 2-chlorobutane 2-bromobutane bromobenzene bromocyclopentane bromocyclohexane Base your explanations on the following considerations: the nature of leaving group, the effect of structure, steric hindrance and any other feature. Be sure to explain which alkyl halides did not react and why1. Rank the list of benzene substituents below from most deactivating to most activating towards electrophilic aromatic substitution. Then clearly indicate for each substituent whether as an ortho/para director or a meta director. -CH3 methyl chloro amide triethylammonium
- Q10. For each of the following reactions (a-b), predict whether the substitution is more likely to occur following an Sn1 or Sn2 mechanism; explain your reasoning. Draw the products of each nucleophilic substitution paying particular attention to the stereochemistry of carbon 1. a) Br, CH3 MeOH H3C b) Br NaOH 1 DMF* H3C *N,N-dimethylformamideConsider disconnecting the following molecule at either bond a, bond b, or bond c. Which of the following answers gives a set of logical synthons that can be converted easily to synthetic equivalents for each disconnection? OMe A OMe OMe OMe OH он OMe OMe OMe OH es/34667/quizzes/36891/take OMe OMe OMe OMe OMe OMe OB OCIdentify whether the following mechanism is SN1, SN2, E1, E2, or E1cB or a combination. a. b. C. d. Br benzyl bromide Br benzyl bromide NaOEt in dry alcohol water in formic acid solution 3-iodocyclohexan-1-one 1-iodo-2,2-dimethylbutane NaOEt in EtOH Aa NaSCH3 OH E
- 2 For each of the following, circle the correct choice to indicate (i) if the substituent would activate or deactivate benzene in EAS reactions (ii) is an ortho/para director or a meta director in EAS reactions. a. b. d. di f. g. h. P Substituent Activating or Deactivating (circle one) Activating -CH; है -OH CEN CH3 -Br -N-CH3 CH3 CH₂ -CH₂ CH₂ & CH₂ Deactivating Activating Deactivating Activating Deactivating Activating Deactivating Activating Deactivating Activating Deactivating Activating Deactivating Activating Deactivating Activating Deactivating Directing Effect (circle one) Ortho/para Meta Ortho/para Meta Ortho/para Meta Ortho/para Meta Ortho/para Meta Ortho/para Meta Ortho/para Meta Ortho/para Meta Ortho/para MetaNonconjugated B,y-unsaturated ketones are in base-catalyzed equilibrium with their conjugated a,ß-unsaturated isomers. The mechanism of interconversion involves the formation of a resonance-stabilized intermediate with three resonance contributors. Draw the structures of these three resonance contributors. OH • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate resonance structures using the symbol from the drop-down menu. + *** Sn [F5. Suggest a plausible arrow pushing reaction mechanism for the following transformation. For any carbocation intermediates formed during the course of reaction mechanism, briefly denote any key stabilization effect(s) based on our discussions in class (i.e. ß-metal cation). You do not need to consider the stereochemical outcome of the reaction. Ph Ph R H me & Of HO Acid Ph OH Ph