Question

1) Arrange the following compounds in the order of de creas ing pKa values. Explain он CH-он CH300H он SH "ОН ООн 2) Construct the energy diagram for rotation of the central (i.e. C2-C3) C-C bond in 2-methyl- butane. Draw Newman projections and wedge-dash structures of all eclipsed and staggered con- formations 3) a) Draw two chair conformations of (1R,3R)-3-methylcy clohex an- 1-ol. b) Draw two chair conformations of the diastereomer of this compound, and name it c) Draw any structural isomer of this compound, and name it

If someone could answer and explain the answer as simply as possible I would greatly appreciate it!

Answer 1

CH, 004 > to Y CHOH > LOH> - electron withdrawing groups like carbonyl cd, makey to groups, dissou ate the 0-H bond e pKq decreases - + m. E. groups like -OCH3 + I.E. groups like - CH2 decreases the dissociation of 0-H. bond and increases the pka - S-H bond dissociates faster than 0-H bond because of less electronegativity of 's'

1) 대 cttz et TH CH3 도 1 도 2 나 | 내 , | 0

I = Ill I = - I = v = fully eclipsed partially eclipsed Gauche a staggered Energy to so is the same in angle to) 2.0

conformations chair PH b) diastereomers of (a)

cyclohexyl methyl ether