Benzylic carbocation

is more stable
Meso compound, drawing
one isomer is fine!
 Chem 14D Fall 2019 Midterm 1 Full Name: ___________

Page 7 of 10 UID: ______ Lec: ___

(c)
1) HC-Na, Et2O

0
2) PhCOCI, AIC1 3
► ►

1) Cy2BH, THF 0
2) H 2O 2 , NaOH, H 2O
3) Cr0 3, cone. H 2 SO 4,
H 2O ' Acetone

(d)

O
I) 0s04 (I equiv), THF OH

2) HzS OH

<) {) � / l)cJV\ .
CN

,_) .b�C.

CN
3) �\:.t"'&J , t.MJ.._. w�
Dt:k...v- any number ofsteps

(>-t-·H•�Cl.-1"1 fCl l.l � �

Cl

Several other correct

possibilities!
Several correct possibilities!