UF CHM2210 Exam #1 Questions with correct answers
alkane + Br2 - ✔✔More substituted carbon, bromine favors tertiary position
alkane + Cl2 - ✔✔racemic mixture Cl on secondary carbon
alkene + HBr - ✔✔racemic mixture where Br is on the more substituted carbon
alkene + HBR/BPO - ✔✔bromine on the less substituted carbon
alkene + H2SO4/H2O - ✔✔[acid catalyzed hydration] Racemic mixture where OH
group goes on the most substituted carbon
alkene + Br2/CHCl2 (draw mechanisms - ✔✔racemic mixture of vicinal Br groups
anti to each other; mechanism includes a bridge of bromine between two carbons
from alkene
alkene + Hg(OAc2)*H2O/NaBH4 - ✔✔forms alcohol on the more substituted
carbon, racemic mixture
alkene + BH3, THF/ H2O2, NaOH - ✔✔forms alcohol on less substituted carbon
alkene + OsO4, H2O - ✔✔syn addition of two alcohols on each carbon
alkene + O3, (CH3)2S ; draw mechanism - ✔✔(ozonolysis) mechanism: slice the
double bond in half, both sides become aldehydes
, alkene + H2/catalyst - ✔✔forms an alkane
alkene + Cl2/H2O (draw mechanism) - ✔✔mechanism: intermediate forms a
bridge with the Cl; Product: racemic mixture where the ROH goes on the more
substituted C and the halogen goes on the less substituted C
alkene + X2, H2O/ NaH, H2O (draw mechanism) - ✔✔mechanism: bridge forms
with halogen and breaks to have alcohol on the most substituted and halogen on
less.
Product: epoxy forms between the carbons from the alkene
alkene + MCPBA/ CH2Cl2 - ✔✔racemic mixture forms when the epoxy forms with
the carbons from the alkene
alkene + CH3OH/H+ - ✔✔ether forms on the most substituted C forming a
racemic mixture
alkyne + NaNH2 - ✔✔deprotonated alkyne and Na cation
alkyne + NaNH2/ CH3X - ✔✔extend carbon chain with a methyl group onto
deprotonated C
alkyne + HgSO4, H2SO4/ H2O (draw mechanism) - ✔✔Mechanism: forms a bridge
between the two carbons in the alkyne, enol (alcohol on a C in an alkene bond)
forms on most substituted carbon.
Product: forms a ketone on the more substituted carbon
alkane + Br2 - ✔✔More substituted carbon, bromine favors tertiary position
alkane + Cl2 - ✔✔racemic mixture Cl on secondary carbon
alkene + HBr - ✔✔racemic mixture where Br is on the more substituted carbon
alkene + HBR/BPO - ✔✔bromine on the less substituted carbon
alkene + H2SO4/H2O - ✔✔[acid catalyzed hydration] Racemic mixture where OH
group goes on the most substituted carbon
alkene + Br2/CHCl2 (draw mechanisms - ✔✔racemic mixture of vicinal Br groups
anti to each other; mechanism includes a bridge of bromine between two carbons
from alkene
alkene + Hg(OAc2)*H2O/NaBH4 - ✔✔forms alcohol on the more substituted
carbon, racemic mixture
alkene + BH3, THF/ H2O2, NaOH - ✔✔forms alcohol on less substituted carbon
alkene + OsO4, H2O - ✔✔syn addition of two alcohols on each carbon
alkene + O3, (CH3)2S ; draw mechanism - ✔✔(ozonolysis) mechanism: slice the
double bond in half, both sides become aldehydes
, alkene + H2/catalyst - ✔✔forms an alkane
alkene + Cl2/H2O (draw mechanism) - ✔✔mechanism: intermediate forms a
bridge with the Cl; Product: racemic mixture where the ROH goes on the more
substituted C and the halogen goes on the less substituted C
alkene + X2, H2O/ NaH, H2O (draw mechanism) - ✔✔mechanism: bridge forms
with halogen and breaks to have alcohol on the most substituted and halogen on
less.
Product: epoxy forms between the carbons from the alkene
alkene + MCPBA/ CH2Cl2 - ✔✔racemic mixture forms when the epoxy forms with
the carbons from the alkene
alkene + CH3OH/H+ - ✔✔ether forms on the most substituted C forming a
racemic mixture
alkyne + NaNH2 - ✔✔deprotonated alkyne and Na cation
alkyne + NaNH2/ CH3X - ✔✔extend carbon chain with a methyl group onto
deprotonated C
alkyne + HgSO4, H2SO4/ H2O (draw mechanism) - ✔✔Mechanism: forms a bridge
between the two carbons in the alkyne, enol (alcohol on a C in an alkene bond)
forms on most substituted carbon.
Product: forms a ketone on the more substituted carbon
