The following synthesis requires more than one step. Specify the reagents you would use to carry it out. (Specify reagents using letters from the table, first reagent on the left. Example: ab) (Notice that there are two possibilities given: NaNH,, and NaNH, in combination with water.) Reagents available a. Brz e. D20 b. 3 NaNH2 / NH3 then H2O r 2 NaNH2/ NH3 c. NANH2/ NH3 d. CH, CH,CH2 Br g. CH3CH2I The reagents are (in order of use):

Choose the most likely regiochemical outcome for the reactants and conditions shown below: 1. BH;THF 2. NaOH, H,O2 Markovnikov with rearrangement C anti-Markovnikov with rearrangement C anti-Markovnikov C None of the choices are correct. C Markovnikov

The synthesis above can be performed with some combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation). Be sure to consider stereochemistry and regiochemistry. А. HBr B. Br2, CCI4 C. Br2, light D. NaCCH E. HBr, ROOR F. NANH2 G. Na, NH3 H. CH3CH,Br

Q5. A. Complete the incomplete reactions. Also write stepwise mechanism for the given reactions. CH3 i. BH3, THE ii. H2O2, HO Br H20 ii. H3C OH H. H3C Br Br2, H20 CH3 Br OH organic solvent CH3 КОН CI V. + CHCI3 KCI CI

Heck reactions take place with alkynes as well as alkenes. The following conversion involves an intramolecular Heck reaction followed by an intermolecular Heck. Work out the reaction sequence on a separate sheet of paper, and then draw the structure of the palladium-containing intermediate A. 1% mol Pd(OAc)₂2 CO₂Me 4% mol Ph P CH₂CN A (1 ring) C (2 rings) (2 rings) • Consider E/Z stereochemistry of alkenes. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Use R1 to represent the palladium complex. The R group tool is located in the charges and lone pairs drop-down menu. 0- ✪ Sn [F MeO₂C

What is the reagent for this transformation?

5. Propose a synthesis of each of the following compounds using the indicated starting material. You may use any organic compounds, inorganic compounds, organometallic compounds, or solvents of your choice. Do not show any reactive intermediates, mechanisms, or transition states, but be sure to show each isolable compound along your synthetic route. a. b. C. Ph + PPh3 Cl mylom Ph. CH3 steps steps steps H3C. H3C Ph CH3 CH3 Ph OH ÕH Ph (racemic) 4