An alcohol ‘B’ when treated with conc. H2SO4 gives compound ‘C’. compound ‘C’ when reacted with Hydrogen bromide produces compound ‘D’. compound ‘D’ when reacted with sodium in presence of ether gives C4H10. i) Write the chemical reactions for the conversion of B to C, C to D and D to C4H10. ii) Write the IUPAC names of the compound B, C and D
Answers
Answer:
Two primary alkyl halides with molecular formula C
4
H
9
Br are possible. They are n-butyl bromide and isobutyl bromide.
When (a) is reacted with sodium metal it gives compound (d), C
8
H
18
which is different from the compound formed when n-butyl bromide is reacted with sodium. Hence, compound a is isobutyl bromide and compound d is 2,5-dimethylhexane.
2CH
3
CH
2
CH
2
CH
2
Br+2Na
Wurtz reaction
CH
3
CH
2
CH
2
CH
2
CH
2
CH
2
CH
2
CH
3
(n−octane)
2CH
3
CH(CH
3
)CH
2
Br+2Na
wurtz reaction
CH
3
CH(CH
3
)CH
2
CH
2
CH(CH
3
)CH
3
(2,5−dimethylhexane)
(a) reacted with alcoholic KOH to give compound (b).
CH
3
CH(CH
3
)CH
2
Br
alcKOH
CH
3
C(CH
3
)=CH
2
(2−methyl−1−propene)
Compound (b) is reacted with HBr to give (c) which is an isomer of (a).
CH
3
−C(CH
3
)=CH
2
HBr
Markownikoff
′
s rule
CH
3
−CBr(CH
3
)CH
3
(tert−