Organic Chemistry II exam with correct solutions
H2, Pd/C - **🔰 VERIFIED ANSWERS🔰 ✔✔C=C --> C-C; ketone --> secondary ROH;
aldehyde --> primary ROH; NO2 --> NH2; CN--> NH2; imine --> NH2; 1 eq. will selectively
reduce a C=C before a C=O, but excess will reduce both
HNO3, H2SO4 - **🔰 VERIFIED ANSWERS🔰 ✔✔Adds NO2 to Benzene (nitration)
H2SO4, heat; H2O, heat - **🔰 VERIFIED ANSWERS🔰 ✔✔1. addition of SO3H to
benzene (sulfonation)
2. removes SO3H from benzene (desulfonation)
Cl2, AlCl3 - **🔰 VERIFIED ANSWERS🔰 ✔✔add Cl to aromatic ring (halogenation); can
also use Br2 and AlCl3; EAS
Br2, FeBr3 - **🔰 VERIFIED ANSWERS🔰 ✔✔add Br to aromatic ring (halogenation); can
also use Cl2 and FeCl3; EAS
RCOCl, AlCl3 - **🔰 VERIFIED ANSWERS🔰 ✔✔adds a carbonyl group directly to
benzene (Friedel-Krafts Acylation)
RCl, AlCl3 - **🔰 VERIFIED ANSWERS🔰 ✔✔adds an R group directly to benzene
(Friedel-Krafts Alkylation); Carbocation Rearrangement
Zn(Hg), HCl - **🔰 VERIFIED ANSWERS🔰 ✔✔reduces carbonyl to an alkane using acid
(Clemmenson Reduction)
H2NNH2,-OH, heat - **🔰 VERIFIED ANSWERS🔰 ✔✔reduces carbonyl to an alkane
using a base (Wolff-Kishner Reduction)
, Sn, HCl, -OH - **🔰 VERIFIED ANSWERS🔰 ✔✔reduces nitrobenzene to aniline with
intermediate (NO2 --> NH3+ --> NH2)
NaNO2, HCl - **🔰 VERIFIED ANSWERS🔰 ✔✔converts PhNH2 --> PhN2 (aniline -->
aryldiazonium salt)
CuCl - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhCl; allows you to add a
halogen para as opposed to halogenation which gives 2 products: ortho and para
CuCN - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhCN
KI - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhI (Iodobenzene)
HBF4 - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhF (Flourobenzene)
H3PO2 - **🔰 VERIFIED ANSWERS🔰 ✔✔reduction of PhN2 --> benzene
H2O, warm - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhOH (Phenol)
KMnO4, acid - **🔰 VERIFIED ANSWERS🔰 ✔✔PhCH3 --> PhCOOH; can also use
NaCr2O7; reacts with any R group with hydrogens on its benzylic carbon to form benzoic
acid; tertiary R group --> No Reaction
NBS, hv - **🔰 VERIFIED ANSWERS🔰 ✔✔adds a Br to the benzylic carbon; adds a Br to
an alkane; PhCH2R --> PhCH(Br)R
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H2, Pd/C - **🔰 VERIFIED ANSWERS🔰 ✔✔C=C --> C-C; ketone --> secondary ROH;
aldehyde --> primary ROH; NO2 --> NH2; CN--> NH2; imine --> NH2; 1 eq. will selectively
reduce a C=C before a C=O, but excess will reduce both
HNO3, H2SO4 - **🔰 VERIFIED ANSWERS🔰 ✔✔Adds NO2 to Benzene (nitration)
H2SO4, heat; H2O, heat - **🔰 VERIFIED ANSWERS🔰 ✔✔1. addition of SO3H to
benzene (sulfonation)
2. removes SO3H from benzene (desulfonation)
Cl2, AlCl3 - **🔰 VERIFIED ANSWERS🔰 ✔✔add Cl to aromatic ring (halogenation); can
also use Br2 and AlCl3; EAS
Br2, FeBr3 - **🔰 VERIFIED ANSWERS🔰 ✔✔add Br to aromatic ring (halogenation); can
also use Cl2 and FeCl3; EAS
RCOCl, AlCl3 - **🔰 VERIFIED ANSWERS🔰 ✔✔adds a carbonyl group directly to
benzene (Friedel-Krafts Acylation)
RCl, AlCl3 - **🔰 VERIFIED ANSWERS🔰 ✔✔adds an R group directly to benzene
(Friedel-Krafts Alkylation); Carbocation Rearrangement
Zn(Hg), HCl - **🔰 VERIFIED ANSWERS🔰 ✔✔reduces carbonyl to an alkane using acid
(Clemmenson Reduction)
H2NNH2,-OH, heat - **🔰 VERIFIED ANSWERS🔰 ✔✔reduces carbonyl to an alkane
using a base (Wolff-Kishner Reduction)
, Sn, HCl, -OH - **🔰 VERIFIED ANSWERS🔰 ✔✔reduces nitrobenzene to aniline with
intermediate (NO2 --> NH3+ --> NH2)
NaNO2, HCl - **🔰 VERIFIED ANSWERS🔰 ✔✔converts PhNH2 --> PhN2 (aniline -->
aryldiazonium salt)
CuCl - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhCl; allows you to add a
halogen para as opposed to halogenation which gives 2 products: ortho and para
CuCN - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhCN
KI - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhI (Iodobenzene)
HBF4 - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhF (Flourobenzene)
H3PO2 - **🔰 VERIFIED ANSWERS🔰 ✔✔reduction of PhN2 --> benzene
H2O, warm - **🔰 VERIFIED ANSWERS🔰 ✔✔substitutes PhN2 --> PhOH (Phenol)
KMnO4, acid - **🔰 VERIFIED ANSWERS🔰 ✔✔PhCH3 --> PhCOOH; can also use
NaCr2O7; reacts with any R group with hydrogens on its benzylic carbon to form benzoic
acid; tertiary R group --> No Reaction
NBS, hv - **🔰 VERIFIED ANSWERS🔰 ✔✔adds a Br to the benzylic carbon; adds a Br to
an alkane; PhCH2R --> PhCH(Br)R
Madison - **🔰 VERIFIED ANSWERS🔰 ✔✔The best neice in the whole entire world
ever!!! :)
