Question

1) Draw the major product of the following intramolecular reaction.

OCH3 1. NaOCH3 کلی۔ OCH3 C9H1205 H3CO 2. H30*

2) Draw the major product of the following reaction that begins with a retro-aldol, followed by an intramolecular aldol condensation.

3) Determine and draw the structures of compounds A and B only. Do not draw the structure of compound X. Place each structure above its letter. HINT: Both A and B are esters.

4) Draw a curved arrow mechanism for the following acid-catalyzed isomerization reaction. You must show all intermediates.

Answer 1

HCO: 6) H осн Solution 02 ORGANIC TRANSFORMATION MECHANISM >> CH₂ D Naocha HC octh strong to 30:27 :03 CH₂O acidle (H 6 3 bashe YE mos: :0:53 OCH SCH ام) OCH OCH Р. с. 3 Kiably resonance stabilised OCH enolate carbonion НА OCH Intra- molecular HC Biboy! My-attack Carbon susceptible On Carbon 20:6) HCO to Intramolecular enolate Murattack Ś mero bered Stronges leguing 0 11 Carbon byelised product OCH group me 0:2 0 'Man CH₂ON9 HCO Hall 3 eca O осн och OCH, Final Reaction (Cahi206] Product

OH OH the dep bond (Retro) (11001] eleavage 7 2 at Electrophilic Musite site B I strong Base 0:6 ou : co) BH H دبی 03 I 8 9 both are lotra equivalent enolates molecular :04 رہ کAle soon Mersite electropbille site 0:6) B-H add conjugak O Tenone H-OH membered Cyclised conjugated Major (Thermodynamic NIS CHOO н Product H IHS HO oot RAS Minor product thermodynamically less favorable

Qis be OEL 3 Anal Product lart compounds 19 Retroanalysis A order to identify and 6 we must can Final product of the OEH Herr centre & Nao El O EL 10:0 CH 2 CH₂ , Br Electrophile Base IX TA OEL a cleavage alfa- bond Nicocleophile synthon -leeto ester Electrophile Cynthoz -a el H OEL 2-Methylpropanoyl chlonde B strongly Group acidie 1 Loft g OH Stronges leaving *?HO (acid- conjugate is aud 2 Ethyl proplonate $ A stronger 10:0 Det KOEL A OEL DA → 1780 La fonaO BI 11 CH₂ Br oEE