X-i The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B HBr, ROOR D HBr 1) xs NaNH2 2) H₂O E H₂, Lindlar's catalyst C 1) 03 2) DMS F t-BuOK

Propose reagents for letters A through D. Write your answer in the space provided, using the letter to denote each set of reagents (A = reagents; B = reagents; etc.). B NH₂ A OH OH D 0= OEt

Give the necessary reagents in the correct order, as a string of letters.

Propose an efficient synthesis for the following transformation: OH H. The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A NaOH 1) MeMgBr; 2) H3O* Na2Cr2O7, H2SO4, H20 t-BUOK F G H. H2, Lindlar's cat. 1) O3; 2) DMS TSCI, py dilute H2SO4 K 1) LIAIH4; 2) DMP or PCC 1) EtMgBr; 2) H3O* 1) BH3-THF; 2) H2O2, NaOH H3O*

OH A The transformation above can be performed with some combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. Br2 D 1) xs NaNH2; 2) H2O G HBr, ROOR Reagent(s): 2 B TsCl, pyridine E conc. H₂SO4, heat H Br t-BuOK C NaOMe F HBr 1 H2, Lindlar's cat.

2

Which ones will be used?

Identify the reagents that can be used to accomplish the following transformation: COOH The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A. 1) Br2, NaOH; 2) H3O+ B. excess NH3 C. 1) O3; 2) DMS D. PCC or DMP E. SOCI 2 F.H3O+

Draw the structures of the products or starting materials I-M in the transformations given below (mechanisms and by-products are not required). но OH PhSe H2SO4 Bu3SnH Me Me Me J Ме AIBN heat HO-O .CI Ph. HN3 `NH -K L HCI N3 t-BUOH M heat MeO2S 'N'

Identify reagents that can be used to achieve the following transformation: OH The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as “EBF"). If there is more than one correct solution, provide just one answer. A В Mel Br2 HC=CNa D E F TSCI, pyridine H2, Lindlar's catalyst Na, NH3 (1) G 1) xs NaNH2 2) H2O 1) O3 2) DMS t-BUOK