3. Propose syntheses of the following two targets beginning with the indicated starting material. 013 HO OH Тон Target #1 Target #2

3. Fill in the boxes to propose syntheses for the following molecules. OH

3) Consider the synthesis below. Identify P1 and deduce What are the reagents/reactants A and B A NH₂ A = B P1 B ii) Zn/(Hg) HC1 HN Br

Choose reagents to convert 2-cyclohexenone to the following compounds. Syntheses may require several steps. Use letters from the table to list reagents in the order used (first at the left). i 1. Li(CH2=CH)2Cu Reagents a 1. Li(CH3)2Cu 2. H3O+ e 1. Li(C6H5)2Cu 2. H3O+ b 1. NaBH4 f CH2l2/Zn(Cu) / ether j 2. H3O+ C NH3 / KOH g 1. CH3MgBr/dry ether k 2 H3O+ d H2NNH2/KOH h HN(CH3)2 HO CH3 a) b) OH N(CH3)2 2. H3O+ (C6H5)3P+-CH2 H₂ over Pd/C KMnO4/H3O+

Chemistry CH3 o-nitrotoluene CH3 NH CI NO2 NH,HCO, 10% Pd/C Step 1 1) NaOAc, H₂O ayla CI CH3 o-toluidine NH3*,CI CH3 CI 4 2-chloro-N-o-tolilpropanami 2) Step 2 2 o-toluidine assignment I need complete mechanism IZ

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Select the appropriate reagent from the reagent bank to accomplish each step in the reactions below. Reaction 1: Reaction 2: Reaction 3: Reaction 4: G Reaction 1 НО. Reaction 2 lo Reaction 3 iOH OH Reaction 4 CN NH₂ ? ? . ? ? НО. loh OH lot NH₂ HO 1) BH3THF 2) H3O+ A HNEt₂ E 1) Et₂CuLi 2) H₂O I mCPBA M Reagent Bank ta NaH B HCI H₂O F HNEt₂ Trace H+ J SOCI₂ N CH3OH H* C 1) EtMgBr 2) H₂O G H₂C=PPh3 K H₂NEt Trace H* O 1) LIAIH4 2) H₂O D 38 НО. H* H -OH H* L DCC OH P

Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.

Choose reagents to convert 2-cyclohexenone to the following compounds.

In both examples below the reactants shown are combined to bring about a nucleophilic substitution (SN1, Sn2) and/or elimination (E1, E2) reaction. What is the major reaction that takes place in each case? CH3 NaOCH2CH3 CH,CH,CCH3 CH;CH,OH SN2 E2 mixture of SN1 and E1 NaSCH3 CH3OH CH2I