Question

8) (11 pts) a) Write out thc 3-step arrow pushing mechanism showing how cthyl propanoate is hydrolyzed in the presence of I mole equivalent NaOH to form sodium propanoate and ethanol. b) H/HO also serve to hydrolyze an ester; brielly explain why NaOH HO is generally preferable. 10) (8 pts) Fill in the missing reagents in cach of the following reductions. More than one step may be required. For + racinho HO + NaOH e come to Na + HO heat 11) (10 pts) Draw the most stable chair conformation for the all cis-isomer of 1,2,3-cyclohexanetriol shown, clearly showing the equatorial and axial groups on cartons 1, 2, and 3. How many stereocenters does this compound have? How many stereoisomers are possible? 9) (10 pts) The hydrobromination of 2-methyl-1-butene could theoretically lead to 2 different alkyl bromides; in practice only one product is formed. Draw the structure of both theoretical products, circle the one that is actually produced, and briefly explain why only one product forms. 12) (6 pts) What question were you hoping would be on the final but was not? State any one question related to Organic Chemistry and answer it.

Answer 1

QUESTION NO 12 is not appropriate for me to answer but questions on oxidation mechanism of alcohols can also be asked. In Question 9 the product can be predicted by Markovnikov's rule.In Question 10 the second reaction involves two steps first reduction to primary alcohols by LiAlH4 and then addition of 1 equivalent of Pyridinium chlorochromate (PCC) will give desired product.

blution + NGOH H₂O A Mat oH unstable telimination of to group e. LAH. Nat 6) Hydrolysis with H+46 ie acidic hydroly is also a viable option but alkaline hydrolysis is preferred because of its kinetics and its yield. Alcaline hydrolysis is faster process and has higher yield compared to acidic hydrolys or (4+140)

OP - This is most stable chair conformer for the 1,2,3 stereoisomer cis cyclohexanetriol only one is possible.

9 HAY Addition H-X • usatostitution - uneymmetrically substituted alkenes is governed by the stability of its intermediate. The intermediate formed in these reaction s is a carbocation and in theoretical productes the intermediate formed are in both cases i same due to stability of carbocation. FI33 Intermediate Nably oth on 1) LEATH 2) 1 eq. of PGC Q