1.

Find out the number of product including stereo

Me H+ / H3O+ H+ / H3O+

OMDM OMDM
Me C CH
HBO HBO
(i) (ii)

H+ / H3O+ H+ / H3O+

OMDM OMDM

HBO HBO
(iii) (iv)

Me CH2
H+ / H3O+ H+ / H3O+

OMDM OMDM

HBO HBO
(v) (vi)

Me H+ / H3O+
(i) BD 3 . THF
OMDM (ii) H2O2

HBO (i) Hg(OAc) 2 , MeOH

(ii) NaBD4 , HO-
(vii) Me (viii)

OMDM & HBO E-1 / 12

2. Find out the product of the given following reaction :

(i) BH3 . THF

(ii) H2O2, HO-
(i) BH3 . THF
CH2
(ii) H2O2, HO-
(i) (ii)

(i) BH3 . THF (i) 9 - BBN

-
(ii) H2O2, HO (ii) H2O2, HO-
(iii) (iv)

(i) BH3, THF (i) BH3, THF

Me C CH - R C C R
(ii) H2O2, HO (ii) H2O2, HO-
(v) (vi)

(i) BH3, THF (i) BH3, THF

- C CH
(ii) H2O2, HO (ii) H2O2, HO-
(vii) (viii)

Me

(i) BH3, THF

(ii) H2O2, HO-
(ix)

OMDM & HBO E-1 / 12

 ANSWER KEY

1.
Me OH Me OH H H
Me Me
OH OH

(b) (c)
(a)

(i) Enantiomeric pair

O O O
Me
Me Me Me Me H
(ii) (a) (b) (c)

OH OH OH

(iii) (a) (b) (c)

OH
OH

OH
(a) (b) (c)
(iv)

OH
OH
OH
2
2 =4

(a) (b) (c)

(v)

(vi)
OH OH OH
(a) (b) (c)

OMDM & HBO E-1 / 12

 OH Me OH OH OH Me Me
Me Me Me H H
OH OH

Me Me Me Me Me Me
(a) (b) (c)

(vii) Diastereomeric pair Diastereomeric pair Diastereomeric pair

(viii)
OH D D OMe
(a) (b)

2.
Me
OH
Me OH

O
Me
HO OH
(i) Me (ii) (iii) (iv) (v) H
Me
O O
OH
CH2-R(vii) OH
(vi) R (viii) (ix)

OMDM & HBO E-1 / 12