ACS Organic Chemistry I & II
Reactions Reagents, and
Functional Groups
Comprehensive Questions
(Frequently Tested) with
Verified Answers Graded A+
Alkyl - Answer: An alkane missing a hydrogen
Aromatic compound - Answer: Cyclic, planar, with every atom of the aromatic ring having a p
orbital, while obeying hackles rule of 4n+2 pi electrons
Vinyl - Answer:
Hydrolysis Reaction - Answer:
Carboxylic Acid - Answer: pKa ~ 5
Enantiomers - Answer: stereoisomers that are non super imposable mirror images
,Diastereomers - Answer: - Same molecular formula, same bond connections, NOT mirrors
images, NOT the same compound.
Stereocenter - Answer: sp3 hybridized and bounded to different subsitutents
Chiral - Answer: objects with non-superimposable mirror images; 'handedness'
Meso - Answer: Achiral compound that contains stereocenters
Cahn-Ingold Prelog - Answer: R/S Nomenclature
E2 - Answer: 3⁰ with strong base, 2⁰ with strong base, 1⁰with strong, non-nucleophilic base
E1 - Answer: 3⁰ with weak base in polar, protic solvents, 3⁰ in polar, protic solvents, with poor
nucleophiles, 2⁰ with poor nucleophiles in polar, protic solvents
SN2 - Answer: 1⁰ with strong bases, 1⁰with weak bases, 2⁰ with weak bases
SN1 - Answer: 2⁰ or 3⁰ in weak bases or poor nucleophiles in polar, protic solvents
CH₃OK/CH₃OH - Answer: Favors SN2 or E2
Acetone - Answer: SN2
OH⁻ - Answer: Nucleophilic Displacement Reaction
Nucleophile - Answer:
, Electrophilic Additions - Answer: Attracted to C=C because of it being oxygen rich
Forms a carbocation intermediate that rearranges to a more stable carbocation that is
immediately susceptible to nucleophilic attack, completing the addition to the double bond.
Attack is on most stable carbon.
CH₃OH/H⁺ - Answer: The H⁺ attacks first. The oxygen of the methanol is the nucleophile
NaH - Answer: ROH to RO- Na+
NaBH4, MeOH - Answer: Ketone to alcohol
H2/Pt - Answer: Reducing to cis
1. LAH 2. H2O - Answer: Reducing to trans
1. RMgX 2. H2O - Answer: Add R group
TMSCl, Et3N - Answer: Protection group of alcohols
TBAF - Answer: Remove alcohol protecting group
1. TsCl, py 2. NaBr - Answer: Make water good leaving group. The sn2
SOCl2, py - Answer: Chlorination of alcohol
H2SO4, heat - Answer: Elimination
Reactions Reagents, and
Functional Groups
Comprehensive Questions
(Frequently Tested) with
Verified Answers Graded A+
Alkyl - Answer: An alkane missing a hydrogen
Aromatic compound - Answer: Cyclic, planar, with every atom of the aromatic ring having a p
orbital, while obeying hackles rule of 4n+2 pi electrons
Vinyl - Answer:
Hydrolysis Reaction - Answer:
Carboxylic Acid - Answer: pKa ~ 5
Enantiomers - Answer: stereoisomers that are non super imposable mirror images
,Diastereomers - Answer: - Same molecular formula, same bond connections, NOT mirrors
images, NOT the same compound.
Stereocenter - Answer: sp3 hybridized and bounded to different subsitutents
Chiral - Answer: objects with non-superimposable mirror images; 'handedness'
Meso - Answer: Achiral compound that contains stereocenters
Cahn-Ingold Prelog - Answer: R/S Nomenclature
E2 - Answer: 3⁰ with strong base, 2⁰ with strong base, 1⁰with strong, non-nucleophilic base
E1 - Answer: 3⁰ with weak base in polar, protic solvents, 3⁰ in polar, protic solvents, with poor
nucleophiles, 2⁰ with poor nucleophiles in polar, protic solvents
SN2 - Answer: 1⁰ with strong bases, 1⁰with weak bases, 2⁰ with weak bases
SN1 - Answer: 2⁰ or 3⁰ in weak bases or poor nucleophiles in polar, protic solvents
CH₃OK/CH₃OH - Answer: Favors SN2 or E2
Acetone - Answer: SN2
OH⁻ - Answer: Nucleophilic Displacement Reaction
Nucleophile - Answer:
, Electrophilic Additions - Answer: Attracted to C=C because of it being oxygen rich
Forms a carbocation intermediate that rearranges to a more stable carbocation that is
immediately susceptible to nucleophilic attack, completing the addition to the double bond.
Attack is on most stable carbon.
CH₃OH/H⁺ - Answer: The H⁺ attacks first. The oxygen of the methanol is the nucleophile
NaH - Answer: ROH to RO- Na+
NaBH4, MeOH - Answer: Ketone to alcohol
H2/Pt - Answer: Reducing to cis
1. LAH 2. H2O - Answer: Reducing to trans
1. RMgX 2. H2O - Answer: Add R group
TMSCl, Et3N - Answer: Protection group of alcohols
TBAF - Answer: Remove alcohol protecting group
1. TsCl, py 2. NaBr - Answer: Make water good leaving group. The sn2
SOCl2, py - Answer: Chlorination of alcohol
H2SO4, heat - Answer: Elimination
