2.2 Draw all the important resonance contributors for the arenium ions formed from each of these molecules when reacted with Br2 and FeBr3 and use this information to decide whether the substituent is ortho/para or meta directing. OH b) N(CH3)2 Ô NH CH3
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- 1 (a) In the following reactions, CI (1) LIAIH, A (2) H20 MCPBA (i) Draw the structure of compounds A and B. (ii) For each reaction, explain the type of reaction involved. (iii) Explain the successful transformation of compound A using mass spectra. (b) Complete the following reactions by filling in missing reactants or product. (i) (1) O3 (2) CH;SCH3 (ii) он (CH3)3(COOH) D Ti(OCH(CH3)2l4 (-)-DET4. For each of the following substituted benzenes below, answer the following questions: ( h) [1] C6H5Br [2] C6H5CN [3] C6H5OCOCH 3 a.) Does the substituent donate or withdraw electron density by an inductive effect? b.) Does the substituent donate or withdraw electron density by a resonance effect? c.) On balance, does the substituent make a benzene ring more or less electron rich than benzene itself? d.) Does the substituent activate or deactivate the benzene ring in electrophilic aromatic substitution?Compare the conformational profile of butane (A) with that of 1,2-dibromoethane (B) While the methyl group is significantly larger than the bromine substituent, butane is found as a mixture of 72% anti and 28% gauche conformers, while compound B consists of 89% anti and 11% gauche conformer. Br Br B A Explain this observation non-verbally.
- 5. a) The hydrogens labeled in the structure below have different acidities. Assign the correct hydrogen to the following pK₁ values. (i) (ii) (iii) (iv) pKa 16 pKa=26 pka=45 pKa=62 A CI 1 B 2 Br H. H b) Circle the hydrocarbon that would have the lowest heat of hydrogenation. H c) Rank the following alkyl halide in order of increasing reactivity in an SN1 mechanism (1 being the least and 4 being the most reactive: H 3 CI D A CI(i) () ВН3, THF B (ii) H202/HO (ii) Br SH Br2 C D (ii) POCI3 CH-CHз Рyridine HO' E (iv) (i) R2BH (ii) H2O2, HO LL(13) Provide the IUPAC name of the following molecule (don't forget the stereocenters). an Br
- 4. Which of the following are not likely products of the reaction below? CH₂ xa OH (A) (B) (C) (D) (E) CH3 H₂SO4 heat Both (B) and (D) Both (A) and (C) Both (C) and (E) Both (D) and (E) (A), (B), and (C) (A) (B) CH₁ (C) CH₂ (D) CH3 (E) CH3(ii) Draw the product R, including a detailed reaction mechanism for the conjugate addition reaction between the 1,3-dicarbonyl P and the a,ß-unsaturated ketone Q. Eto P OEt + Q OEt Et3N R (iv) Explain why conjugate addition is favoured over direct addition to Q in this case.5. a) The hydrogens labeled in the structure below have different acidities. Assign the correct hydrogen to the following pK₂ values. (i) (ii) (iii) (iv) pKa=16 pka=26 pKa=45 pKa=62 A 2 B H 1- H b) Circle the hydrocarbon that would have the lowest heat of hydrogenation. Br H X X c) Rank the following alkyl halide in order of increasing reactivity in an SN1 mechanism (1 being the least and 4 being the most reactive: H ot 3 D 4
- Consider the reaction between (1S,3S)-1-chloro-3-methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. -SH C NaOH Draw only the organic product. Select /// Draw Rings More C H S Erase:The pka of phenol (C6H5OH) is 10.0. When a nitro group (NO2) is attached to the ring, the pK, decreases, as shown for the ortho, meta, and para isomers. OH OH ОН OH NO2 (a) Explain why the pK, values of all three isomers are lower than the pka of phenol itself. (b) Explain why the meta isomer has the highest pka of `NO2 Phenol NO2 the three isomers. pKa = 10.0 7.23 8.35 7.14Which of the following would accomplish the transformation below? a) 1. HSCH2CH2SH, H+; 2. H2, Raney Ni b) H2N-NH2, NaOH(aq), heat c) H2, Pd d) All of the above