Question

please explain why and how they are E2/SN2/SN1/E1

3. Draw a structural formula for the major organic product(s) of each reaction and specify the mechanism by which each product is formed (SNI, S2, El, or E2). • NaOH H20 CH,CH ON CH,CH OH CH ON CH,OH CH OH Na DMSO

Answer 1

The substra SN pathway: - The leaving group beside on the 3°(tebiay) carbon atom 30 (tentary soy The SN2 reaction pathway puled out. Because the higher the stenic hinderance lowen child be the rate of the SN? - heaction... SO, SN?_pathaway ruled out. The remaining ane- SNI, E',E? Elch SN':- A8 8H is strong base nather Han a good nucleophile (because of " Highen charge density.on oxygenatom) hase) and to reaction neutral bang/ & Mecleophile tend to go through SNlOnE SI SN and El buled out The substrates is tetiary and have change Nude ophile so, the beaction child phocceeds through E2-pathway: . The major product of the beaction. fa Mae not a neutraal Nudekile base) (Magoh Phoduct) highly substitueted alker

SNL pathcoyob El pathway :- As the substrate in (10 che primary 10 (primary canbon) aften cabben) the formation of cabbocation (1²) the stability of carbocation alill be very less. sol the beaction with this substrates Neithen follow Elons N' battiway. (As we know the formation of stable canbocation is the bate determining step for shoh E). So, ElandsN pathway hule dout SNon E2_pathways The Base po nucleophile is given is CH₂ CH₂ - 8 and this is Strong base hatter than a good neucleophile and SN? eaction pheffen a good nucleophil not the strong bone like CH3-CH₂-8 so, SN2 bathway huled out. The heaction will go E² puthaway. H I CH3CH2 & Maps A

CN (Pheftoned conformation both in ejuitonton tch the 30 (teniany canbon atom) As the nucleophile is cH₂8 (changed species) so, SNI El huled out (The heason ane given in the above disscussion] NOW SN? --/ the approach of the nucleophile from the above of the cyclohexyl system and at the time of approaching CH₂8 min face - stebis hindenence with the iso propyl group. So,SNP-heaction buled out CH8 Mat Now, This beaction goes through E²-pathway. the marked Hydrogen is antion with leaving group a so this chill abstract by the cH38

* Y (majoh Bb Io (3oob tähtiany -CH3 carobon) LCH3 The CH3OH is neutral so it is a good Nucleophile bather than a strong bone and the cabbon centre in tertiany 2, SM? - pathway ruled out. Stl pathway in Bb CH3CH ② CH₃ Steps LCH3 LCH R-D) (stable cabbocation CH3GH CH₃ l 1H 6cH₃olange Эno + 11 OCH (majon) (minolo) les stable due to 1,3-dianial intenaction with 2 H and targer ghoup - OCH3 (langer than's -CH3) Et-pathaway fouled out because WCH₃OH in a good nucleophile not a strong bone.

OTS - As the solvent in DMSO ('polan apnotic) it chill follow eithersH²chE?. 20 (secondany Canber) E² pathway's I cha £8 ion is not a strong base I due to hesonance. so it is a good CH3-6- nucleophile. and (ressonaling E-pathway bulled Structunes) out. DO The substrate cuith 20 (secondary canbon) and a good nucleophile it will undergo beaction throug SN2 pathaway. ROTS T SOTS invension 030 C2- SOCH CH3 Transition state) OTA CH3 (invemion product) (majont