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Question

Propene (CH3CH=CH2) can be transformed to compound (a to j) listed in the left-hand column.
Write letter designating the reagent, you believe will achieve desired transformation. In the case of a multi step sequence, write the reagent in the order they are to be used.

Desired productNo. of StepsWrite options
Reagent List
a.CH3CHBrCH2Brone
A.Hg(OAc)2 in H2O
b.(CH3)2CHOHtwo
B.B2H6 in THF
c.CH3CH2CH2OHtwo
C.NaBH4 in alcohol
d.CH3COCH3three
D.Br2 in CH2Cl2
e.CH3CH2CHOthree
E.H2O2 in aqueous base
f.CH3CH(OH)CH2Brone
F.HOBr(NBS in aqueous acetone)
g.(CH3)2CHBrone
G.HBr in CH2Cl2
h.CH3CH(OH)CH2OHtwo
H.OsO4 in ether
i.CH3CH2CH2Clthree
I.Thionyl chloride (SOCl2)
j.CH3CCHtwo
J.NaHSO3 in aqueous acetone
K.NaOH in alcohol and reflux
L.NaNH2 (strong base)

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Solution

Solution:-

Desired productNo. of Steps Write options Reagent
a.CH3Br|CHCH2Brone D A. Hg(OAc)2 in H2O
b.(CH3)2CHOHtwo AC B. B2H6 in THF
c. CH3CH2CH2OHtwo BE C. NaBH4 in alcohol
d. CH3COCH3three ACF D. Br2 in CH2Cl2
e. CH3CH2CHOthree BEFE. H2O2 in aqueous base
f. CH3OH|CHCH2Brone F F. HOBr (NBS in aqueous state)
g. (CH3)2CHBrone G G. HBr in CH2Cl2
h. CH3OH|CHCH2OH two HJ H. OsO4 in ether
i. CH3CH2CH2Clthree BEI I. Thionyl chloride
j. CH3CCHtwoDL J. NaHSO3 in aqueous acetone
K. NaOH in alcohol and reflux
L. NaNH2 (Strong base)

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