DAT Bootcamp Organic Chemistry Tests #3, #6, and #10 Complete Practice Questions Latest Updated Page 1 2026-03-13
DAT Bootcamp Organic
Chemistry Tests #3, #6, and
#10 Complete Practice
Questions Latest Updated
Guidehttps://www.stuvia.com/dashboard!@_)#*)(@$)($@*($@)($@*_ 1
Page 1 of 38 DAT Bootcamp Organic Chemistry Tests #3, #6, and #10 Complete Practice Questions Latest Updated.pdf
,DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3 Page 2 2026-03-13
Addition of a bromine to an alkene (Bromination) in nonnucleophilic solvent such as CCl4 gives
Vicinal dibromide
When you see that a solution is in acid when looking at a reaction with an epoxide,
always add the substituent to the more substituted side
Page 2 of 38 2 DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3.pdf
,DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3 Page 3 2026-03-13
Addition of a bromine to an alkene (bromination):
The reaction proceeds through a cyclic intermediate and with the bromine atoms adding on opposite sides (the
product has an anti stereochemistry). The reaction does not pass through a free carbocation, so rearrangements are
never observed and the reaction is highly stereospecific. Thus, bromination of a 3-methylcyclohexene produces
compound B and its enantiomer.
vicinal
refers to the relationship between two functional groups that are attached to adjacent carbon
Geminal
refers to the relationship between two functional groups that are attached to the same carbon
Page 3 of 38 3 DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3.pdf
, DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3 Page 4 2026-03-13
Types of dihalides
The rate determining step in SN1 involves
breaking of the carbon halogen bond, and formation of a carbocation.
Tertiary alkyl halide
will be most reactive toward *SN1* because it forms the most stable carbocations. Tertiary carbocations are stabilized
by hyperconjugation
If the high priority substituents are on the same side of the double bond, they are labelled
Z
Page 4 of 38 4 DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3.pdf
DAT Bootcamp Organic
Chemistry Tests #3, #6, and
#10 Complete Practice
Questions Latest Updated
Guidehttps://www.stuvia.com/dashboard!@_)#*)(@$)($@*($@)($@*_ 1
Page 1 of 38 DAT Bootcamp Organic Chemistry Tests #3, #6, and #10 Complete Practice Questions Latest Updated.pdf
,DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3 Page 2 2026-03-13
Addition of a bromine to an alkene (Bromination) in nonnucleophilic solvent such as CCl4 gives
Vicinal dibromide
When you see that a solution is in acid when looking at a reaction with an epoxide,
always add the substituent to the more substituted side
Page 2 of 38 2 DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3.pdf
,DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3 Page 3 2026-03-13
Addition of a bromine to an alkene (bromination):
The reaction proceeds through a cyclic intermediate and with the bromine atoms adding on opposite sides (the
product has an anti stereochemistry). The reaction does not pass through a free carbocation, so rearrangements are
never observed and the reaction is highly stereospecific. Thus, bromination of a 3-methylcyclohexene produces
compound B and its enantiomer.
vicinal
refers to the relationship between two functional groups that are attached to adjacent carbon
Geminal
refers to the relationship between two functional groups that are attached to the same carbon
Page 3 of 38 3 DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3.pdf
, DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3 Page 4 2026-03-13
Types of dihalides
The rate determining step in SN1 involves
breaking of the carbon halogen bond, and formation of a carbocation.
Tertiary alkyl halide
will be most reactive toward *SN1* because it forms the most stable carbocations. Tertiary carbocations are stabilized
by hyperconjugation
If the high priority substituents are on the same side of the double bond, they are labelled
Z
Page 4 of 38 4 DAT Bootcamp orgo Test #6, Orgo Test 10, Organic chemistry test 3.pdf
