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1. Draw the synthons and synthetic equivalents formed by cleaving the indicated bond. (24 pts) synthons synthetic equivalents2. Circle the most acidic hydrogen(s) in the molecule. (8 pts) O Η T O Ι Η Η H, Α. -cΞc-}, Η. H Η Η Η Η Η Η3. Determine the pK, for each type of hydrogen in the molecule. Write the number above the line for each type of hydrogen. (14. Draw an arrow pointing to the most basic atom in each molecule. (8 pts) a. b. OCH,5. Show the synthesis of the target molecule. You may use benzene, potassium cyanide, and chloromethane as your only sources

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1 cal OH H-Ć - CH₂ CH3 CH₂ CH₂ CH₃ Il disconnect OH Synthons: @CH2 CH₂ CH3 H-C-CH 2 CH₃ Synthetic equivalents: O CHE-CH₂ CH3CECHz CH₃ Synthons Sipathetic equivalente ince + Bringets OH OH d) Synthons tc. C- CH - CH3 - He- c - in O-CH₂ CH₂ CH3 HOCH ₃

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