Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Which of the following reaction sequences can be used to achieve the transformation shown below? Reaction Sequences:
Options
- ASequences 2 and 3
- BSequences 1 and 2
- CSequences 1 and 3
- DSequences 1, 2 and 3
Correct answer
B. Sequences 1 and 2
Step-by-step solution
The transformation requires converting benzyl alcohol ( C₆H₅CH₂OH ) to benzylamine ( C₆H₅CH₂NH₂ ) without changing the number of carbon atoms. In Sequence 1: C₆H₅CH₂OH PBr₃ C₆H₅CH₂Br N₃^- C₆H₅CH₂N₃ [H₂O] LiAlH₄ C₆H₅CH₂NH₂ This yields the correct product. In Sequence 2: C₆H₅CH₂OH PCC C₆H₅CHO NH₃ C₆H₅CH=NH H₂, Pd/C C₆H₅CH₂NH₂ This yields the correct product. In Sequence 3: C₆H₅CH₂OH PBr₃ C₆H₅CH₂Br CN^- C₆H₅CH₂CN [H₂O] LiAlH₄ C₆H₅CH₂CH₂NH₂ This yields 2-phenylethanamine, which has an extra carbon atom. Therefore, only