UTA ORGANIC CHEMISTRY I
(BUGARIN) - TEST TWO EXAM
QUESTIONS AND ANSWERS 100% PASS
2026/2027
When treated with a nucleophile, an alkyl halide undergoes a _____ reaction where the
nucleophile replaces the halogen. - ANS Substitution
When treated with a base, an alkyl halide undergoes a _____ reaction where a pi bond (double
bond) is created. - ANS Elimination
In summation: SN2 reactions - ANS Strong nucleophile; primary/methyl substrate; polar
aprotic solvent; inversion of configuration
In summation: SN1 reactions - ANS Weak nucleophiles; tertiary substrate; polar protic solvent
(hydrogen bonding); retention of configuration (racemization)
In summation: E2 reactions - ANS Strong base (big molecule); tertiary substrate; polar aprotic
solvent; requires transferrable proton and leaving group to be anti-periplanar.
In summation: E1 reactions - ANS Weak base; tertiary substrate; polar protic solvent;
produces unequal mixes of enantiomers
@2026 ALLRIGHTS RESERVED 1
,How does the induction effect created by a halide encourage a reaction? - ANS The greater
electronegativity of the halide withdraws electron density of the adjacent carbon atom and
renders it electrophilic.
Good leaving groups are the _____ of strong acids with pKa < 0 - ANS Conjugate bases
Repeat: The stronger the acid, the weaker the conjugate base and and the better said base
functions as a leaving group. - ANS The stronger the acid, the weaker the conjugate base and
the better said base functions as a leaving group.
Weak bases are the most _____ - ANS Stable bases
Identify the alpha position of an alkyl halide. - ANS Carbon atom directly attached to halogen.
Only one in a molecule.
Identify the beta position of an alkyl halide. - ANS Carbon atoms attached to the alpha
carbon.
What do the beta positions of an alkyl halide signify? - ANS Whether the alkyl halide is
primary (1 R-group), secondary (2 R-groups) or tertiary (3 R-groups)
SN2 and E2 reactions feature _____ mechanisms - ANS Concerted; both nucleophilic
attacks/proton transfers and loss of the leaving group occur in a single step
SN1 and E1 reactions feature _____ mechanisms - ANS Stepwise; the steps occur with a
carbocation intermediate.
@2026 ALLRIGHTS RESERVED 2
, Concerted reactions are _____ because they involve the simultaneous collision of molecules -
ANS Bimolecular
What happens in an SN2 reaction where the alpha position is a chiral center? - ANS The
configuration is inverted, which requires that the nucleophile must attack from the backside.
Why can nucleophiles only attack from the backside of the molecule? - ANS Because
according to MO theory, electron density flows from HOMO to the LUMO; at the front, a node
will be encountered and the lack of an overlap prevents the reaction.
SN2 and E2 reactions are said to be _____ because the configuration of the product is
dependent on the configuration of the starting material. - ANS Stereospecific
The rate of an SN2 reaction is very sensitive to the presence of _____ - ANS Constituents at
the alpha or beta positions, which slow the reaction. Alpha substituents are more harmful to
the rate.
SN2 reactions occur with _____ substituents - ANS Primary or methyl
SN2 reactions cannot progress with ____ substituents - ANS Tertiary
SN1 reactions occur with ____ substituents - ANS Tertiary
SN1 reactions cannot progress with ____ substituents - ANS Primary
For secondary constituents, one must examine the _____ - ANS Configuration and the nature
of the solvent.
@2026 ALLRIGHTS RESERVED 3
(BUGARIN) - TEST TWO EXAM
QUESTIONS AND ANSWERS 100% PASS
2026/2027
When treated with a nucleophile, an alkyl halide undergoes a _____ reaction where the
nucleophile replaces the halogen. - ANS Substitution
When treated with a base, an alkyl halide undergoes a _____ reaction where a pi bond (double
bond) is created. - ANS Elimination
In summation: SN2 reactions - ANS Strong nucleophile; primary/methyl substrate; polar
aprotic solvent; inversion of configuration
In summation: SN1 reactions - ANS Weak nucleophiles; tertiary substrate; polar protic solvent
(hydrogen bonding); retention of configuration (racemization)
In summation: E2 reactions - ANS Strong base (big molecule); tertiary substrate; polar aprotic
solvent; requires transferrable proton and leaving group to be anti-periplanar.
In summation: E1 reactions - ANS Weak base; tertiary substrate; polar protic solvent;
produces unequal mixes of enantiomers
@2026 ALLRIGHTS RESERVED 1
,How does the induction effect created by a halide encourage a reaction? - ANS The greater
electronegativity of the halide withdraws electron density of the adjacent carbon atom and
renders it electrophilic.
Good leaving groups are the _____ of strong acids with pKa < 0 - ANS Conjugate bases
Repeat: The stronger the acid, the weaker the conjugate base and and the better said base
functions as a leaving group. - ANS The stronger the acid, the weaker the conjugate base and
the better said base functions as a leaving group.
Weak bases are the most _____ - ANS Stable bases
Identify the alpha position of an alkyl halide. - ANS Carbon atom directly attached to halogen.
Only one in a molecule.
Identify the beta position of an alkyl halide. - ANS Carbon atoms attached to the alpha
carbon.
What do the beta positions of an alkyl halide signify? - ANS Whether the alkyl halide is
primary (1 R-group), secondary (2 R-groups) or tertiary (3 R-groups)
SN2 and E2 reactions feature _____ mechanisms - ANS Concerted; both nucleophilic
attacks/proton transfers and loss of the leaving group occur in a single step
SN1 and E1 reactions feature _____ mechanisms - ANS Stepwise; the steps occur with a
carbocation intermediate.
@2026 ALLRIGHTS RESERVED 2
, Concerted reactions are _____ because they involve the simultaneous collision of molecules -
ANS Bimolecular
What happens in an SN2 reaction where the alpha position is a chiral center? - ANS The
configuration is inverted, which requires that the nucleophile must attack from the backside.
Why can nucleophiles only attack from the backside of the molecule? - ANS Because
according to MO theory, electron density flows from HOMO to the LUMO; at the front, a node
will be encountered and the lack of an overlap prevents the reaction.
SN2 and E2 reactions are said to be _____ because the configuration of the product is
dependent on the configuration of the starting material. - ANS Stereospecific
The rate of an SN2 reaction is very sensitive to the presence of _____ - ANS Constituents at
the alpha or beta positions, which slow the reaction. Alpha substituents are more harmful to
the rate.
SN2 reactions occur with _____ substituents - ANS Primary or methyl
SN2 reactions cannot progress with ____ substituents - ANS Tertiary
SN1 reactions occur with ____ substituents - ANS Tertiary
SN1 reactions cannot progress with ____ substituents - ANS Primary
For secondary constituents, one must examine the _____ - ANS Configuration and the nature
of the solvent.
@2026 ALLRIGHTS RESERVED 3
