Interpretation: Using a Gabriel synthesis, a given primary amine compound has to be synthesized.
Concept Introduction:
The general formula for primary amine is –NH2. There are several methods available to prepare primary
Formation of potassium phthalimide (deprotonation)
Potassium phthalimide in alkaline KOH acts as the reagent which has negatively charged phthalimide. It is formed by the reaction between phthalimide and potassium hydroxide.
Formation of R−N bond by SN2 nucleophilic substitution
The negative charged nitrogen atom in phthalimide can easily attract the positive side of R−X. In primary
Formation of primary amine by hydrolysis
The resultant product further goes for hydrolysis using hydrazine as the reagent. This reaction also follows nucleophilic substitution reaction. Finally, primary amine is formed with a side product of hydrazine derivative.
To find: Using a Gabriel synthesis, prepare the given primary amine compound
Identify the correct alkyl halide involved in the formation of the given compound

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Chapter 22 Solutions
ORGANIC CHEMISTRY-PRINT MULTI TERM
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- Show the mechanism for these reactionsarrow_forwardDraw the stepwise mechanismarrow_forwardDraw a structural formula of the principal product formed when benzonitrile is treated with each reagent. (a) H₂O (one equivalent), H₂SO₄, heat (b) H₂O (excess), H₂SO₄, heat (c) NaOH, H₂O, heat (d) LiAlH4, then H₂Oarrow_forward
- Draw the stepwise mechanism for the reactionsarrow_forwardDraw stepwise mechanismarrow_forwardPart I. Draw reaction mechanism for the transformations of benzophenone to benzopinacol to benzopinaco lone and answer the ff: a) Give the major reason for the exposure of benzophenone al isopropyl alcohol (w/acid) to direct sunlight of pina colone Mechanism For b) Pinacol (2,3-dimethy 1, 1-3-butanediol) on treatment w/ acid gives a mixture (3,3-dimethyl-2-butanone) and 2, 3-dimethyl-1,3-butadiene. Give reasonable the formation of the productsarrow_forward
- what are the Iupac names for each structurearrow_forwardWhat are the IUPAC Names of all the compounds in the picture?arrow_forward1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)arrow_forward
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