ACS Organic Chemistry II Final
Examination and Answers.
What is the IUPAC priority for naming? - Answer Carboxylic acid > Ketone > Aldehyde >
Alcohol
In IUPAC naming, what is the suffix used for ketone groups? - Answer -one
In IUPAC naming, what is the suffix used for alcohol groups? - Answer -nol
In IUPAC naming, what is the suffix used for esters? - Answer -noate
Benzyl group - Answer
Phenyl group - Answer
ethanoic acid - Answer
(E) isomers vs. (Z) isomers. Which one is observed when the higher ranked molecules are on the
same side? opposite? - Answer highest on same side: Z
highest on opposite sides: E
Electron-withdrawing groups are what type of directors? What is the one and only exception? -
Answer Meta (deactivators)
Halogens
If the atom directly attached to the aromatic ring has lone pairs what type of director is it? what
if it does not have lone pairs? - Answer lone pairs: activating, ortho, para director
no lone pairs: deactivating, meta director
When are the terms ortho, meta, para used? - Answer when there are 2 substituents on the
aromatic ring
In IUPAC naming, what is NH2 on a phenyl ring referred to as? - Answer aniline
Analine - Answer
, Amine - Answer
Amide - Answer
If there is a NO2 group present, what IUPAC prefix will also be evident? - Answer nitro
What is the predicted reaction? 1º alkyl halide with a strong base? weak base? poor
nucleophile? - Answer strong base: Sn2 favored but E2 with strong non-nucleophilic bases
weak base: Sn2
poor nucleophile: no reaction
What is the predicted reaction? 2º alkyl halide with a strong base? weak base? poor
nucleophile? - Answer strong base: mostly E2
strong non-nucleophilic bases: mostly Sn2
poor nucleophile: Sn1/E2 (slow) in polar, protic solvents
What is the predicted reaction? 3º alkyl halide with a strong base? weak base? poor
nucleophile? - Answer strong base: E2
strong non-nucleophilic bases: Sn1/E1 in polar protic solvents
poor nucleophile: Sn1/E1 in polar, protic solvents
What is the configuration of the product in the base-catalyzed hydrolysis of (R)-1-choloro-1-
deuteriobutane? - Answer (S)-1-deuterio-1-butanol (Sn2)
Where is the largest molecule on the periodic table? - Answer Bottom lefthand corner
Nucleophilic strength increase with increasing what? - Answer atomic size
Which alkyl valid would you expect to undergo Sn1 hydrolysis most rapidly?
I, Br,Cl, or F? - Answer I
In which reaction is a racemic mixture obtained?
In which reaction is an inversion of chirality obtained? - Answer inversion: Sn2
racemic mix: Sn1
Examination and Answers.
What is the IUPAC priority for naming? - Answer Carboxylic acid > Ketone > Aldehyde >
Alcohol
In IUPAC naming, what is the suffix used for ketone groups? - Answer -one
In IUPAC naming, what is the suffix used for alcohol groups? - Answer -nol
In IUPAC naming, what is the suffix used for esters? - Answer -noate
Benzyl group - Answer
Phenyl group - Answer
ethanoic acid - Answer
(E) isomers vs. (Z) isomers. Which one is observed when the higher ranked molecules are on the
same side? opposite? - Answer highest on same side: Z
highest on opposite sides: E
Electron-withdrawing groups are what type of directors? What is the one and only exception? -
Answer Meta (deactivators)
Halogens
If the atom directly attached to the aromatic ring has lone pairs what type of director is it? what
if it does not have lone pairs? - Answer lone pairs: activating, ortho, para director
no lone pairs: deactivating, meta director
When are the terms ortho, meta, para used? - Answer when there are 2 substituents on the
aromatic ring
In IUPAC naming, what is NH2 on a phenyl ring referred to as? - Answer aniline
Analine - Answer
, Amine - Answer
Amide - Answer
If there is a NO2 group present, what IUPAC prefix will also be evident? - Answer nitro
What is the predicted reaction? 1º alkyl halide with a strong base? weak base? poor
nucleophile? - Answer strong base: Sn2 favored but E2 with strong non-nucleophilic bases
weak base: Sn2
poor nucleophile: no reaction
What is the predicted reaction? 2º alkyl halide with a strong base? weak base? poor
nucleophile? - Answer strong base: mostly E2
strong non-nucleophilic bases: mostly Sn2
poor nucleophile: Sn1/E2 (slow) in polar, protic solvents
What is the predicted reaction? 3º alkyl halide with a strong base? weak base? poor
nucleophile? - Answer strong base: E2
strong non-nucleophilic bases: Sn1/E1 in polar protic solvents
poor nucleophile: Sn1/E1 in polar, protic solvents
What is the configuration of the product in the base-catalyzed hydrolysis of (R)-1-choloro-1-
deuteriobutane? - Answer (S)-1-deuterio-1-butanol (Sn2)
Where is the largest molecule on the periodic table? - Answer Bottom lefthand corner
Nucleophilic strength increase with increasing what? - Answer atomic size
Which alkyl valid would you expect to undergo Sn1 hydrolysis most rapidly?
I, Br,Cl, or F? - Answer I
In which reaction is a racemic mixture obtained?
In which reaction is an inversion of chirality obtained? - Answer inversion: Sn2
racemic mix: Sn1
