CHEM 217 W’23 PS#4

Dr. H. H. Palandoken

PROBLEM SET (PS) #4

(COMPILED FROM OLD EXAMS, QUIZZES)

SYNTHESES
 page 1
SYNTHESIS. Complete the following syntheses using only the reactions that we have learned in CHEM216 (see
CHEM216 Review List on Canvas) and CHEM217 to date. Provide detailed reaction conditions (i.e., all the
requisite reagents and their molar equivalents, solvents, temperature, etc.) and structures of intermediates
for each step required to complete each synthesis.
(a)
TIPSO ? HO
O !
TIPSO HO

(b)
HO

? OH
!

racemic
 page 2

SYNTHESIS. Complete the following syntheses using only the reactions that we have learned in CHEM216 (see
CHEM216 Review List on Canvas) and CHEM217 to date. Provide detailed reaction conditions (i.e., all the
requisite reagents and their molar equivalents, solvents, temperature, etc.) and structures of intermediates for
each step required to complete each synthesis.

(c)
Br
?
!

racemic

(d)

squiggly bond indicates a mixture of R and S

configurations at the asymmetric carbon

?
O ! OCH3

racemic
 page 3

SYNTHESIS. Complete the following syntheses using only the reactions that we have learned in CHEM216 (see
CHEM216 Review List on Canvas) and CHEM217 to date. Provide detailed reaction conditions (i.e., all the
requisite reagents and their molar equivalents, solvents, temperature, etc.) and structures of intermediates for
each step required to complete each synthesis.

(e)
?
!

(f)
?
!
 page 4
SYNTHESIS. Complete the following syntheses using only the reactions that we have learned in CHEM216 (see
CHEM216 Review List on Canvas) and CHEM217 to date. Provide detailed reaction conditions (i.e., all the
requisite reagents and their molar equivalents, solvents, temperature, etc.) and structures of intermediates for
each step required to complete each synthesis.

(g)
? OH
!

(h)
? OH
!
 page 5
SYNTHESIS. Complete the following syntheses using only the reactions that we have learned in CHEM216 (see
CHEM216 Review List on Canvas) and CHEM217 to date. Provide detailed reaction conditions (i.e., all the
requisite reagents and their molar equivalents, solvents, temperature, etc.) and structures of intermediates for
each step required to complete each synthesis.

(i)
D
O ? OH
!

racemic

(j)
D
OD ? OD
!

racemic