I) Ranking the following compounds in decreasing basicity (1 strongest base; 4we

Question

I) Ranking the following compounds in decreasing basicity (1 strongest base; 4weakest base). (0.5 pts) 2) Predict the major organic product for the following reactions. You do not need to draw stereoisomers if formed. (05 pts each) 1) PBr3 2) Mg, ether a) 2-Methyl-1-propanol 3) 4) H provide structure of product 2) H3O+ b) 3) SOCl2 pyridine 4) (CH3)2CHCH2OH, pyridine 1) SOCl2 c) 2) CH3CH2NH2 d) 3) Provide the starting material for the following reaction series. (0.5 pts) 1) H2CrO4, H2SO4 H20 2) SOCl2 (provide starting material) (2 equivalents)

Explanation / Answer

1) Order of basicity is IV > III > I > II

2) Major product formed below are as follows

a- 3-methylbutanoic acid

b- Isobutylbenzoate       c- N-ethyloctahydro-1H-indene-2-carboxamide    d- 2-hydroxybenzoic acid

3) starting material is 4,5-dimethylhexan-1-ol

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