Question

1. (8 points) Draw the ylide that is produced upon reacting each of the following compounds with triphenylphosphine (Ph3P) and then butyllithium (BuLi). If the ylide cannot be produced, explain why. a. (CH3)3CCH2Br b. (CH3)3CBr c. (CH3)2CHCH2Br d. CH3C1 2. (4 points) Most Wittig reactions you find in the literature involve a strong base during the reaction. Why is a base not used in this week's experiment? Can we use an ylide with a free carboxylic acid? Ph2p= OH Php this week's ylide an ylide with a free carboxylic acid 3. (4 points) It is possible to generate sulfur ylides in a manner similar to that used to produce phosphonium ylides. For example, treating a sulfonium salt with a strong base gives the sulfur ylide (shown below).

Answer question 2 please with a full response.

Answer 1

BE + pp — pine But, we no protons at de carbon S UP- - of my I oft stable stable gields directly gjeldy i we can use with out base P- SEL are not stable . Yes, we can use OEL - these anions we w generate insiture. glide with free carboglic and Puli cshs-afty-Br - at - So 8 4 8 - (Sulfur ylide)