What is most likely the initial retrosynthetic step from the target molecule in the given transformation (ie, the last step of the synthesis)? or Br O Elimination of the dibromide to give an alkyne. Addition of Br₂ to a cis alkene. O Free radical bromination with Br₂ O Addition of Br₂ to a trans alkene.

This reaction is an example of conjugate addition of a nucleophile to an a,ẞ-unsaturated carbonyl. O CH3CH2CH2CH=CHCSCOA H₂O OH CH3CH2CH2CHCH2CSCOA Draw the two resonance structures of the enolate anion intermediate for this reaction. • Draw an R1 group in place of COA. The R group tool is located in the charges and lone pairs drop-down menu. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu. ->> 90-87 O + ? ChemDoodle >

Draw the two resonance structures of the enolate anion intermediate for this reaction.

When the cleavage of an ether occurs, in step 2, how come the bromide ion does not attack the carbon on the cyclopentane? How come it attacks the CH2 carbon? Does it matter which one is being attacked?