List the letter that corresponds to the reagent from the reagenttable you need to carry out the following synthesis in 5 steps orless.
Heat may not appear on the reagent table with the reagent, but youcan assume you have a hot plate and can supply neededheat.
There may be more boxes than you need. Type NA in the blank of any extra box(es).
2-ethylbut-1-ene %u2192 2-ethyl-2-methylbutanoic acid
step 1
step 2
step 3
step 4
step 5
Reagents:
A: HCl, 25o
B: Cl2, h%u03BD
C: Br2, h%u03BD, heat
O: SOCl2, pyridine
E: PBr3
X: conc. H2SO4, heat
G: KOC(CH3)3, HOC(CH3)3, heat
EE: H2, Pd
(other metals: Ni, Rh, Pt)
I: HCl, 0oC
J: 50% H2SO4, H2O
M: HBr, 0oC
F: HBr, peroxides or HBr, h%u03BD
RR: 1. B2H6, diglyme 2. H2O2, NaOH or 1. BH3-THF 2.H2O2, NaOH
P: Cl2 or Br2, CHCl3 or CCl4, dark, cool
Q: Cl2 or Br2, H2O
N: peroxyacetic acid
S: 1. O3 2. H2O, Zn or 1. O3 2. HOCH3(CH3)2S
PP: 1. O3 2. H2O
U: KOCH2CH3 HOCH2CH3
V: NaNH2, NH3
GG: 1. 3NaNH2, NH3 2. H2O
HH: H2, Lindlar
II: Na, NH3
QQ: H2SO4, HgSO4
R: NBS, benzoyl peroxide, CCl4, heat
SS: Na, NH3, HOCH3
BB: Na2Cr2O7, H2O, H2SO4, heat
NN: HNO3, H2SO4
OO: Br2, FeBr3 or Cl2, FeCl3
Z: AlCl3
Y: Zn(Hg), HCl
D: H2NNH2, KOH, triethylene glycol, heat
AA: PCC, CH2Cl2 or PDC, CH2Cl2
TT: Mg
CC: Na
DD: OsO4 (cat) (CH3)3COOH,tert-butyl alcohol,NaOH
JJ: HIO4
KK: LiAlH4
LL: NaBH4
H: NaOH, heat MM: ethylene oxide
K: NaCN
L: NaOH
T: aqueous acid
W: CO2
FF: SOCl2