1. Choose the best reagents to carry out the following reaction sequence. Show specific aldehyde or ketone. A. Mg/ether B. RCH=O, aldehydes C. R₂C=O, ketones HOCH₂CH₂OH/H+/heat F. PCC E. D. tBu(CH3)2Si-Cl/Py aka TBDMS-CI/Py H+/H₂O/heat HO ylide G. Br to remove water H. CH3OH/H+ 2. Draw an ylide and carbonyl combination to prepare the following alkene. carbonyl — H3C J. CrO3/H2SO4 H3C OH CH3 CH3 CH3 OH over-

7. Predict the major product or provide the reagents in the following reactions. Be sure to show stereochemistry if necessary. ? CrO3, H2SO4, H20 a. Br HO. acetone b. 1. MgBr 2. H3O* workup с. NABH4 H. MeOH d. Br Mg, Et,0 MeOH

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Choose the best reagents to complete the reaction shown below. HBr А 1. LIAIHA 2. H30* 1. NaBH4 2. H30* 1. H30* D 2. PhMgBr 1. PhMgBr E 2. H30* Version: 1.0.94 + production B.

Specify the reagent you would use in each step of the following synthesis: OH step 1 step 2 Reagents Available a. LIAIH4 f. PBr3 k. CH;CH,MgBr b. H2SO4 g. pyridinium chlorochromate (PCC) I. CęH5MgBr (phenylmagnesium bromide) c. HCI h. NaH m. (CH3)2CHMgBr d. HBr i. NaOH n. Cro3 e. SOCI2 j. CH3M9B Write the letters of the reagents in the boxes below. Reagent for step 1 Reagent for step 2

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Draw the product of each reagn

Starting materials Br Reagents OH 1 H3C OH 2 Br 6 Br 7 OH OH TOH OH 8 5 H a Mg / dry ether e Aqueous H2SO4 at reflux i KMnO4 / H3O+ b 1. CO2 2. acidic workup of Conc. HCI or HCI (gas) j Na2CrO4 / aqueous H2SO4 C NaCN/THF or DMF g PBr3 K 1. BH3/THF 2. H₂O2/aq. NaOH d NaCN/dil. aqueous H2SO4 h KOH alcohol |

12. Which reagents/conditions would lead to the transformation depicted below in high yield? a. NaOMe, MeOH b. MeOH, H₂O* c. NaOEt, EtOH 13. In the structure of 2-fluoropropanoic acid shown, the oxidation number on C1 is the oxidation number on C2 is a. +1, +2, -3 b. -3, +1, +3 d. NaOH, H₂O e. two of these , and the oxidation number on C3 is, c. 0, 0, 0 d. +3,0,-3 e. +2,0, -2 ??? OH 14. What will be the outcome of the following reaction sequence? B. 1. NaOEt, EtOH 2. PCC 3. isopropylMgBr 4. H₂0¹ ??? a. 2-ethyl-3-isopropyl-2,3-dimethyloxirane b. 2,3,4-trimethyl-3,4-epoxyhexane c. 1,2,3,4-tetramethyl-2,3-epoxypentane d. Both a and b are suitable. e. All of the above are correct. OH 15. What is a suitable IUPAC name for the structure shown at the right? OH D. F H OH LOH CH3 3 OH

Specify the reagent you would use in each step of the following synthesis: CI step 1 step 2 H. Reagents Available a. LIAIH4 f. PBr3 k. CH;CH,MgBr b. H2SO4 g. Dess-Martin periodinane (DMP) 1. CgHgMgBr (phenylmagnesium bromide) с. НС! h. NaH m. (CH3)2CHMgBr d. HBr i. NaOH n. Cro3 e. SOCI, j. CH3MGB Write the letters of the reagents in the boxes below. Reagent for step 1 Reagent for step 2| An error has been detected in your answer. Check for typos, miscalculations etc. before submitting your answer.