Question 4. Predict the most likely site of electrophilic aromatic substitution in each compound below. If you think there will be a major and minor product, identify both. Briefly explain the reason(s) that you made your choice. Rank the three compounds in increasing order of reactivity (number them as 1,2 and 3 being the most reactive). S SI S
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- 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-dimethylformamideQ10. 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. а) Br CH3 MeOH H3C b) Br NaOH DMF* H3C *N,N-dimethylformamide2. For each of the nucleophilic substitution reactions below (a-d), place a box around the most nucleophilic atom, circle the most electrophilic atom, and draw a straight arrow to point to the leaving group. Then predict the main carbon containing product of each reaction, drawing its line structure showing stereochemistry using wedges and dashes, if appropriate. Predict the type of mechanism: circle SN1 or SN2. a. b. C. d. e. Br + Na CEN Br →→ CI + Na N=N=N (NaN3) Za H CI + O-H Sigla Na CH3 (+ + Na S-CH3 water SN2 SN1 SN2 SN1 SN2 SN1 SN2 SN1 SN² SN1
- 9) Suppose I want to perform a simple substitution reaction, replacing the OH with a Cl in the following compound. Which of the following reagents works best? Explain (and that means explain why the wrong answers are wrong as well as why the right answer is right). Option A: Addition of HBr Option B: Addition of SOC12/pyridine Option C: Addition of SOCl2 only OH ? J1The following compounds are treated with HNO3/H2SO4. Predict the positions of electrophilic attack that lead to the major nitration product(s). (Enter each possible nitration position as an alphabetical letter string without commas or spaces, i.e. ab or abd. Enter the string in alphabetical order.) H3C. b 1. a Br OH 2. CENReagents. Provide reagents for the following transformations, A - H. In some cases, there are multiple correct answers. If there are two steps indicate this with a 1.), 2.), etc. [Pay close attention to the direction of the arrows!] H SH HO G В OH E HS Br ОН OH ОН A: E: В: F: С: `G: D: H:
- b).. .. Under each potential product of this E2 elimination, write "major product," "minor product," or "not formed." Me Br H Me Me OH Me Ph Ph H Me H Et Me Me Me Ph Ph Me Me EtDraw the major product obtained when the following alkyl halide undergoes an E2 reaction. If you expect no reaction to occur, submit the starting material as your answer. Interactive 3D display mode CH3 CI Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. + L H 2D EXP. CONT. H C2) For each compound below, identify the atom most likely to be attacked first by a nucleophile and identify the unoccupied frontier orbital (e.g. p, í*, or o*) associated with that atom. A O CI B N- -N C D N-O H
- 4. Predict the major product and propose a mechanism for the following reaction. Include intermediates, correct formal charges, and all arrows involved in the mechanism. Br₂4. For the following reaction scheme, please convert the starting material to the corresponding product. If the reaction is destined to fail, please write "no reaction" to the right, otherwise draw the appropriate product to the right of the arrow. NABH4 MeOH 1. LİAIH4 Meo 2. H20 OMe 1. CH3MgBr (excess) 2. H2О 1. C6H5LI (excess) 2. НаоConsider the following substitution reaction, where X represents an alkyl bromide: X substitution product of the four alkyl bromides below, one will not react. The other three will react at varying rates. Put the compounds in order based on which will react fastest in the above reaction. Fastest reaction: t (1) Br CH₂OH (2) Br H₂C-Br (3) :slowest reaction Br (4) Won't react: