1.

Identify the reagents necessary to accomplish each of the following transformations shown here:

Choose from the following list of reagents:

Choose from the following list of reagents:

a 1) Br2 2) xs NaNH2 3) H2O

b 1) MeMgBr 2) H3O+

c H2, Pt

d PCC, CH2Cl2

e 1) EtMgBr 2) H3O+

f dilute H2SO4

g 1) R2BH 2) H2O2, NaOH

h Na2Cr2O7 H2SO4, H2O

i NaOH

j t-BuOK

k H2, Lindlar's catalyst

l HBr, ROOR

m 1) TsCl 2) t-BuOK

n 1) BH3THF 2) H2O2, NaOH

o 1) LiAlH4 2) H3O+

p PBr3

2. Propose an efficient synthesis for the following transformation

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		C		D
t-BuOK		HBr, ROOR		Na2Cr2O7, H2SO4, H2O		HBr
E		F		G		H
H2, Lindlar's cat.		1) O3; 2) DMS		TsCl, py		dilute H2SO4
I		J		K		L
1) LiAlH4; 2) H3O+		DMP or PCC		conc. H2SO4, heat		1) MeMgBr; 2) H3O+

3.

Propose an efficient synthesis for the following transformation:

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		C		D
t-BuOK		1) MeMgBr; 2) H3O+		Na2Cr2O7, H2SO4, H2O		NaOH
E		F		G		H
H2, Lindlar's cat.		1) O3; 2) DMS		TsCl, py		dilute H2SO4
I		J		K		L
1) LiAlH4; 2) H3O+		DMP or PCC		1) EtMgBr; 2) H3O+		1) BH3THF; 2) H2O2, NaOH

. . H CH . , . CH2 OH . . .. Br . - H