Organic Chemistry II Exam 1 Study Guide With complete
solu on RATED A+ 2025/2026 NEW!!
-0.5 to 15.0 ppm
What is the H NMR chemical shi range?
-5 to 220 ppm
What is the 13C NMR chemical shi range?
electron density of each proton and carbon in the molecule
What do chemical shi s in H and 13C NMR reflect?
upfield shi
More electron density
downfield shi
less electron density
downfield
Electronega(ve elements (O,N, and X) and resonance effects cause _____ effect
homotopic
-iden(cal chemical shi s
-exchange test provides an iden(cal molecule
ex: CH3
enan(otopic
-iden(cal chemical shi s in a chiral environment
-exchange test provides a set of enan(omers
ex: CH2 hydrogens in achiral molecule
diastereotopic
When the molecule has chiral centers, CH2, or isopropyl group
proton chemical shi tendency based on the func(onal groups
D2O
OH hydrogens can be iden(fied by what treatment?
, Proton signal integra(on
(area under the signal) provides the ra(o (#) of hydrogens
spin spin spli6ng
singlet, doublet, triplet
neighboring protons (N+1 rule)
What is the spli6ng pa8ern determined by?
coupling constant (J value)
Neighboring protons have a same what?
Assign proton signals from the structure by looking at chemical shi , integra(on, spli6ng
pa8ern, and J values
Assemble a structure using the NMR data including chemical shi s, spli6ng pa8erns, integrals,
and J values.
Dis(nguish alkene hydrogens based on their chemical shi s
Dis(nguish either cis or trans isomer based on the coupling constant (J values)
Why is the 13C NMR much less sensi(ve than H NMR (natural abundance)
Be able to expect the # of carbon signals from the structure
Be aware of carbon chemical shi tendency for func(onal groups
Be able to assign carbon signals for simple organic compounds.
Understand chemical shi equivalence based on symmetry in the molecule.
Name alkynes using IUPAC
Terminal alkynes are very acidic (pKa 25), and provide alkynyl anion based on the treatment of
strong bases such as alkyl lithium and NaNH2 in liquid ammonia
(1) elimina(on reac(ons
(2) Using alkynyl anion
*SN2 Reac(ons
*Grignard Reac(on
How can you prepare an alkyne?
elimina(on reac(on
solu on RATED A+ 2025/2026 NEW!!
-0.5 to 15.0 ppm
What is the H NMR chemical shi range?
-5 to 220 ppm
What is the 13C NMR chemical shi range?
electron density of each proton and carbon in the molecule
What do chemical shi s in H and 13C NMR reflect?
upfield shi
More electron density
downfield shi
less electron density
downfield
Electronega(ve elements (O,N, and X) and resonance effects cause _____ effect
homotopic
-iden(cal chemical shi s
-exchange test provides an iden(cal molecule
ex: CH3
enan(otopic
-iden(cal chemical shi s in a chiral environment
-exchange test provides a set of enan(omers
ex: CH2 hydrogens in achiral molecule
diastereotopic
When the molecule has chiral centers, CH2, or isopropyl group
proton chemical shi tendency based on the func(onal groups
D2O
OH hydrogens can be iden(fied by what treatment?
, Proton signal integra(on
(area under the signal) provides the ra(o (#) of hydrogens
spin spin spli6ng
singlet, doublet, triplet
neighboring protons (N+1 rule)
What is the spli6ng pa8ern determined by?
coupling constant (J value)
Neighboring protons have a same what?
Assign proton signals from the structure by looking at chemical shi , integra(on, spli6ng
pa8ern, and J values
Assemble a structure using the NMR data including chemical shi s, spli6ng pa8erns, integrals,
and J values.
Dis(nguish alkene hydrogens based on their chemical shi s
Dis(nguish either cis or trans isomer based on the coupling constant (J values)
Why is the 13C NMR much less sensi(ve than H NMR (natural abundance)
Be able to expect the # of carbon signals from the structure
Be aware of carbon chemical shi tendency for func(onal groups
Be able to assign carbon signals for simple organic compounds.
Understand chemical shi equivalence based on symmetry in the molecule.
Name alkynes using IUPAC
Terminal alkynes are very acidic (pKa 25), and provide alkynyl anion based on the treatment of
strong bases such as alkyl lithium and NaNH2 in liquid ammonia
(1) elimina(on reac(ons
(2) Using alkynyl anion
*SN2 Reac(ons
*Grignard Reac(on
How can you prepare an alkyne?
elimina(on reac(on
