(a) Conversion of Fischer Projection to Sawhorse Projection : The transformation of Fischer
projection formula of a compound to sawhorse projection may bé accomplished by first making an
eclipsed form which is then rotated through 180° around C)—C3 bond. This is illustrated by taking ‘
example of 3-bromo-2-butanol.
CH.
J CH, HO, H |
H—+—- 08 p
= CHy OH = HC
u—4 Br
H7 “Br H Br
CH,
Sawhorse projection Sawhorse projection
3-Bromo-2-butanol_ "
Fischer projection) (eatipged forma (staggered form)
In this conversion, the last chiral centre in Fischer projection (counting from the top) may
considered as the front carbon in sawhorse formula.
‘Scanned with CamSeannerprojection may similarly be carried out and is explained in the following f
Isher cHo B ra
! > HL Br q
Nenman HW a
CH,OH CHO
Fischer an BO Newman projection
Projection eclipsed staggered
‘Scanned with CamSeanner(a) Conversion of Fischer Projection to Flying Wedge Representation :
In this conversion, the vertical bonds in Fischer projection are considered to be in the plane of
paper and the horizontal bonds project above and below the plane. For example, the conversion of
Fischer projection of one of the stereoisomers of lactic acid into flying wedge forms (IX and X) m:
be proceeded as follows :
below the
COOH __ group on the = Plane =) fo Wis crt COOH
proup ti ton the
u Bae Fight side aL Hse l OH
x =. 7
vertical Cay above the HO’ ‘CH3 Hc NH
bond 3 plane Ix x
Lactic acid Fischer projection Flying wedge Flying wedge
(® When the vertical bond, bearing the CH3 group in Fischer projection, is bent on the right si
of flying wedge formula (IX), the OH group on the right side in the horizontal bond in Fischer
projection should be written above the plane of the paper (represented by solid cone —=) and the
atom should therefore, be placed below the plane (represented. by broken line ~~) in the flyi
wedge representation.
(ii) If the vertical bond, bearing the CH3 group in the Fischer projection, is bent to the left in th
flying wedge formula (X), the group on the left side in the horizontal bond in Fischer projection is
be placed above (—=) the plane of the paper and the group on the right (H) should be placed belo
(am) the plane. Thus, both IX and X represent the flying wedge forms of Fischer projection of lactic
acid. -
‘Scanned with CamSeanner