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- 2. How suit the (Pb) of product with the molecular weight?4. (5 pts) Extra credit Explain why the "benzyne" reaction (Hint: look at one of the major products) always yields a 50/50 mixture of isomers. A drawing or two would be great!1. (4) a) Predict the product(s) for each of the following reactio b) 2 -OH H r.t. Br₂, H+
- 6. (5 pt) Draw a reasonable curved-arrow mechanism for the reaction below converting the starting material to the product indicated. Be sure to explicitly draw all the lone pairs present on heteroatoms (e.g. O, N, S, Cl etc). Draw out all relevant resonance structures. Check for conservation of charge and conservation of mass. Honor Grossman's Rule. Note: You may disregard stereochemistry for this problem. H H cat HCI, H₂O HO LOH3. Vanillin is one of the components of natural extract from vanilla bean. Draw what you would expect the infrared spectra of vanillin to look like, make sure to include labels for peaks and axes. **Would you expect the IR spectra of ethyl vanillin (-OEt instead of -OCH3 group) to look different? H,CO. HO 0 wavenumber cm H2 (a) In the following reaction, PCC A (i) Draw the structure of compound A. (ii) Explain using the IR spectra to confirm that the reaction is completed. (iii) Identify the molecular ion peak for compound A. (iv) Fragmentation of A shows a peak at m/z 111. Draw the possible cation for this peak. (v) Determine the resonance structure of this cation.
- (4)Rank the following compounds in order of reactivity toward an SÂl reaction. (1-best) CH3CH₂Br H₂C=CHC(Br)CH3 H₂C=CHBr CH3CH(Br)CH32 (a) In the following reaction, OH РСС A (i) Draw the structure of compound A. (ii) Explain using the IR spectra to confirm that the reaction is completed. (iii) Identify the molecular ion peak for compound A. (iv) Fragmentation of A shows a peak at m/z 111. Draw the possible cation for this peak. (v) Determine the resonance structure of this cation.(4)Rank the following compounds in order of reactivity toward an SN1 reaction. (1-best) CH3CH₂Br H₂C=CHC(Br)CH3 H_C=CHBr CH3CH(Br)CH3 2 3
- 7. a) A) In the box below the arrow, label if the pericyclic reaction is a Diels Alder (DA), Electrocyclic (EC) or Sigmatropic Rearrangement (SR). B) Determine the major product(s). heat HO₂C b) heat to c) + 1. Na, NH3 NO2 NO2 2. heatI don't undertaand how you calculated the final ratio of H(2)O at the end of the explaination. How did you come to 6?When n-butylbenzene is ionized by electron-impact ionization in a mass spectrometer, radical cation D initially forms as the molecular ion. It then readily fragments. Which of the following fragments would likely be present in the highest abundance in this mass spectrum relative to the others shown? D (A) (B) (D)