1-bromobutane conversion work shown

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SUMMARY

This discussion focuses on the conversion of 1-bromobutane into various organic compounds, including 1-butyne, octane, and others. The specific reactions outlined include the use of tert-butyl alcohol and potassium tert-butoxide for the synthesis of 1-butyne, and sodium cyanide for the production of butyl cyanide. The user seeks assistance with extending the alkyl halide to octane and deuterating the bromine in the conversion to CH3CH2CH2CH2D. Additionally, the discussion highlights the importance of Wurtz coupling in these transformations.

PREREQUISITES
  • Understanding of organic synthesis reactions
  • Familiarity with alkyl halides and nucleophilic substitutions
  • Knowledge of Wurtz coupling methodology
  • Basic principles of deuteration in organic chemistry
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  • Research the mechanism of Wurtz coupling for alkyl halides
  • Study the process of deuteration using D2O or D3O+
  • Explore methods for synthesizing octane from butyl halides
  • Investigate the use of sodium cyanide in nucleophilic substitution reactions
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Chemistry students, organic chemists, and researchers involved in synthetic organic chemistry and reaction mechanisms.

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equations used to convert 1-bromobutane to:

a.) CH3CH2CH2CH2D

b.) octane

c.) 1-butyne

d.) CH3CH2CH2CH2CN

e.) CH3CH2CH2CH2-O-C-(=O)-CH3


work shown below:

c.) 1-butyne

CH3CH2CH2CH2Br => {(CH3)3COH, (CH3)3COK} =>CH3CH2CH=CH2
CH3CH2CH=CH2 => {Br2} => CH3CH2CHBrCH2Br
CH3CH2CHBrCH2Br => {NaNH2, NH3} => CH3CH2C(bondx3)C(-)Na(+)
CH3CH2C(bondx3)C(-)Na(+) => {H2O} => CH3CH2C(bondx3)CH

d.) CH3CH2CH2CH2CN
CH3CH2CH2Br + NaCN --> CH3CH2CH2CH2CN + NaBr

5. CH3CH2CH2CH2-O-C(=O)CH3

CH3CH2CH2CH2Br + CH3C(=O)OH

I need help with a.) and b.) I don't know how to extend the alkyl halide to an octane, and exchange the Br with D for a)

please help me...
 
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