H₂C CH₂ a: Br₂, CH₂Cl₂ b: NaNH2, NH3 c: CH3CH₂Br d: H₂O, H₂SO4, HgSO4 e. H₂, Lindlar catalyst Select reagents from the table to show how you would carry out this synthesis. Reagents Available H3C f. Li, NH3 (liq) g. CH₂l2, Zn(Cu) h. H₂, Pd/C i. BH3 then H₂O₂ j. HCI, ether CH3 (Enter your answer as a series of letters, i.e. jbc, in the order that you wish to use the reagents. Repeat a letter if you want to use more than one equivalent of the reagent. Do not use commas or spaces.)

Reagent 3 NaBH4 NBS, Persoxides, hv Zn(hg),HCl H2

Provide reasonable step-by-step mechanisms for the following reactions. Use arrows to indicate themovement of electrons.

1. Name the following compounds. OH b. НО, OH а. с. F. NO2 d. HO Br 2. Provide the missing reagent(s) and major product(s) for each of the following reactions. а. Br AIBR3 b. OH HBr с. OH H,PO4 (conc.) A d. Но AICI,

Predict major products for the following reactions g. h. H2SO4 d. e. NaOH A 1. .CI 1. Li(tBu),AIH من 2. H₂O+ 1. LiAlH4 2. H₂O+ 1. DIBAL-H, -78 °C 2. H₂O* 1. LiAlH4 2. H₂O+ 1. LiAlH4 J. OH 2. H₂O*

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

Please don't provide handwritten solution .....

6. Predict the product for the following reaction. "NH₂ Br H₂N NO₂ D. H₂O* A. Fe/HCI IV OH OH Br 11 NH₂ "NH₂ H₂N A. IB. II C. III D. IV E. V 7. Provide the reagents necessary to carry out the following reaction. NH₂ V 1. LIAIH4 2. H₂O NH₂ B. H₂CCOCI C. Br₂/FeBr3 E. dil. Na₂CO3 III

1. Reaction of excess methyllithium with ethyl acetate (CH3CO2C2H5) produces, after acid work-up, ___.     2. Reaction of excess ethyl magnesium bromide with ethyl benzoate (C6H5CO2C2H5) produces, after acid work-up, ___.     3. Reaction of excess ethyl magnesium iodide with ethyl acetate (CH3CO2C2H5) produces, after acid work-up, ___.

Starting Materials CH3B CH3CH2BR CH3CH2CH,Br C6H5Br Reagents Mg, ether 1. a. 2. 13CH2-13C-OH b. 13CO2 then H3O* 3. LIAIH4 then H3o* PBr3 CO2 then H30* C. 4. d. 5. C6HsCH2Br е. Select a starting material and a series of reagents necessary to synthesize this compound in as few steps as possible. Enter your selection as a number for the starting material, followed by the letters of the reagents, in the order that you wish to use them, i.e. 3abcf.