Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following statements is false regarding 1,3-dithiane?
Options
- A1,3-Dithiane can be used for preparing aldehydes and ketones.
- BIt can be alkylated by CH ₃ CH ₂ CH ₂ Br .
- CIt can be alkylated by Me ₂ CHX .
- D1,3-Dithiane can react with RLi .
Correct answer
C. It can be alkylated by Me ₂ CHX .
Step-by-step solution
1,3-Dithiane is a widely used reagent in organic synthesis for the umpolung (polarity reversal) of aldehydes. Let us evaluate the given statements: Statement (A): 1,3-Dithiane can be deprotonated and subsequently alkylated. Upon hydrolysis, the alkylated dithianes yield aldehydes (if alkylated once) or ketones (if alkylated twice). Thus, this statement is true. Statement (D): The hydrogen atoms on the carbon between the two sulfur atoms (C2 position) are acidic ( pK_a 31 ). 1,3-Dithiane reacts with strong bases lik