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Question 044 Which of the following sequences converts 2-methylpropene and sodium acetylide into 3-methylbutanal? 1) HBr; 2) NaCCH; 3) O3; 4) DMS 1) NaCCH; 2) H2/Ni2B; 3) O3; 4) DMS 1) HBr, ROOR; 2) NaCCH; 3) H2/Ni2B 4) O3; 5) DMS 1) HBr, ROOR; 2) NaCCH; 3) O3; 4) H2O 1) HBr; 2) NaCCH; 3) O3; 4) H2O

User Hyralex
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2 Answers

1 vote

Answer:

1) HBr; 2) NaCCH; 3) O3; 4) H2O

Step-by-step explanation:

The first step is formation of alkyl halide followed by reaction with sodium acetylide, to form 3-methylbutene, which is then followed by oxidation reaction with O3& H2O to 3-methylbutanal

User Public Static Void
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3 votes

Answer:

The sequence of reagents' incorporation for the conversion of 2-methylpropene into 3-methylbutanal is option (C.):

1.
HBr,ROOR ; 2.
NaCCH,H_(2)/Ni_(2)B ; 3.
O_(3), DMS

Step-by-step explanation:

The summary of this reaction's mechanism is as follows:

  • Radical hydro-halogenation of 2-methylpropene through a technique known as "peroxide effect" in which the HBr addition causes free radical formation of the alkene
  • Nucleophilic SN2 substitution reaction (acetylide)
  • Hydrogenation
  • Ozonolysis of the alkene: after the addition reaction, the intermediate ozonide is converted to aldehyde using dimethyl sulfide (DMS)
User Alex Maker
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