Chemistry · Organic Reaction Mechanisms
In a reaction sequence where an α,β-unsaturated carbonyl compound is treated with triphenylphosphine (PPh 3 ) and t-butyldimethylsilyl triflate (TBSOTf), followed by n-butyllithium (n-BuLi), an aldehyde, and finally tetra-n-butylammonium fluoride (TBAF), what is the role of TBAF in the final step?
Verified Solution4 OptionsUpdated: October 2026👁️1 View
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- 1Cleavage of the carbon-carbon double bond
- 2Deprotonation of the phosphonium salt to form an ylide
- 3Fluorination of the alkene to form an alkyl fluoride
- 4Deprotection of the silyl ether to regenerate the alcohol group✓
Correct answer
Deprotection of the silyl ether to regenerate the alcohol group
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