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reagent 1 reagent 2 reagent 3 reagent 4 reagent 5 Reagent table A PCC, CH 2 Cl 2

ID: 888644 • Letter: R

Question

reagent 1

reagent 2

reagent 3

reagent 4

reagent 5

Reagent table

A

PCC, CH2Cl2

P

Na (s)

FF

CuBr

B

Na2Cr2O7, aq H2SO4

Q

HNO3, H2SO4

GG

CuCN

C

Mg (s)

R

NaNO2, HCl,H2O, cold

HH

HBF4

D

LiAlH4

S

HIO4

II

H3PO2

E

LiAlD4

T

H2, Pd

JJ

KNH2, NH3

F

NaBH4, HOCH3

U

D2, Pd

KK

KND2, ND3

G

NaBD4, DOCH3

W

H3O+, aqueous acid

(acid workup)

LL

CuI

H

O3

X

D2O

MM

SOCl2

I

OsO4, H2O2

Y

NaOH, H2O

NN

PBr3

J

Ethylene oxide

Z

NaOD, D2O

OO

formaldehyde

K

LDA

lithium diisopropyl amide

AA

Br2,FeBr3

PP

NaCN

L

NaOCH3, HOCH3

BB

Cl2,AlCl3

QQ

NaN3

M

NaOCH2CH3, HOCH2CH3

CC

HBr

RR

H2SO4

N

CO2

DD

HBr, peroxides

SS

NaBH3CN

O

HOCH2CH2OH,

p-toluene sulfonic acid (trace acid)

EE

KI

TT

NaBD3CN

reagent 1

reagent 2

reagent 3

reagent 4

reagent 5

Explanation / Answer

We can convert the bromo benzaldehyde to dueterated benzaldehyde by following four steps

(i) HOCH2CH2OH,p-toluene sulfonic acid (trace acid): For protecion of aldehydic group by formation of cyclic acetal.

(ii) Reagent C : Magnesium : it will give Grignard's reagent of the bromo benzene

(iii) Reagent X: D2O for reduction and replacent by dueterium

(iv) Reagents W: H3O+, aqueous acid (acid workup), for deprotection of aldehydic group by hydrolysis of acetal .

(v) No reagent

(vi) no reagent