Question:

3) Autopsies of soldiers killed in WWII by sulfur mustard gases revealed low white blood cell counts and defects in bone marrow

3) Autopsies of soldiers killed in WWII by sulfur mustard gases revealed low white blood cell counts and
defects in bone marrow development. Through these observations and further research, that these sulfur
mustard gases had profound effects on rapidly dividing cells because of the molecules showed an extemely
strong propensity to undergo nucleophilic substitution reactions.
Provide electron-pushing mechanisms for both steps to account for how the sulfur increases the reactivity of
the alkyl halides of mustard gases using the chemical transformations below. (6 pts)
Nu
internal
Sy2ro
Nu:
Sy2
0
$
16
Based upon the knowledge gained from the study of mustard gases, a huge research effort was undertaken to
determine if this class of molecules could be used against aggressive cancer cells lines (of course, using less
potent mustard gas derivatives!)
One molecule studied is shown below. Using the proposed electron-pushing mechanisms used above, can
you provide an expected product if the nucleophile used was methanol (CH3OH)? Hint: after nucleophilic
substitution, the alcohol is acidic and easily deprotonates to make an ether (4 pts)
CH,OH
14
Further studies showed the mustard gas derivatives investigated had a strong propensity to react with DNA,
especially the nucleobase guanine. Guanine is well known for having a strong nucleophilic nitrogen at
position 7 of its structure. Propose a product structure for this reaction using the provided mustard gas
deriviative and guanine structure. (5 pts)
INH
HO
mah
14
NH2
DNA
Note: The numbering on guanine and other nucleobases is done not necessarily for IUPAC nomenclature. It
is done to be useful in discussion of reactivity at different sites on the nucleobase structure. With 5 nitrogens
and 5 carbons, it makes it a lot easier to say reactivity at N7 versus trying to describe that position on the
cyclic ring... This is done a lot on complex structures.
/14

3) Autopsies of soldiers killed in WWII by sulfur mustard gases revealed low white blood cell counts and defects in bone marrow development. Through these observations and further research, that these sulfur mustard gases had profound effects on rapidly dividing cells because of the molecules showed an extemely strong propensity to undergo nucleophilic substitution reactions. Provide electron-pushing mechanisms for both steps to account for how the sulfur increases the reactivity of the alkyl halides of mustard gases using the chemical transformations below. (6 pts) Nu internal Sy2ro Nu: Sy2 0 $ 16 Based upon the knowledge gained from the study of mustard gases, a huge research effort was undertaken to determine if this class of molecules could be used against aggressive cancer cells lines (of course, using less potent mustard gas derivatives!) One molecule studied is shown below. Using the proposed electron-pushing mechanisms used above, can you provide an expected product if the nucleophile used was methanol (CH3OH)? Hint: after nucleophilic substitution, the alcohol is acidic and easily deprotonates to make an ether (4 pts) CH,OH 14 Further studies showed the mustard gas derivatives investigated had a strong propensity to react with DNA, especially the nucleobase guanine. Guanine is well known for having a strong nucleophilic nitrogen at position 7 of its structure. Propose a product structure for this reaction using the provided mustard gas deriviative and guanine structure. (5 pts) INH HO mah 14 NH2 DNA Note: The numbering on guanine and other nucleobases is done not necessarily for IUPAC nomenclature. It is done to be useful in discussion of reactivity at different sites on the nucleobase structure. With 5 nitrogens and 5 carbons, it makes it a lot easier to say reactivity at N7 versus trying to describe that position on the cyclic ring... This is done a lot on complex structures. /14

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