Question

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