hybridization bond angle hybridization?outlines/… · ch. 1 – bonding, resonance, and molecular...

Ch. 1 – Bonding, Resonance, and Molecular Geometry DAT Organic Chemistry Outline

© DAT Bootcamp 1 of 100|Page

Quiz 1.1 – Molecular Bonding Geometry and Hybridization

1. What is the hybridization and bond angle of each atom indicated?

Quiz 1.2 – Condensed Formulas and Line-Bond Formulas

1. Write the condensed formula for each of the following structures:

H

C

H

H

H H

C

O

H

hybridization?hybridization?

hybridization?

C CH H

hybridization?



Quiz 1.3 – Sigma and Pi Bonds

1. How many sigma (σ) and pi (π) bonds are there in each of the molecules below?

Quiz 1.4 – Orbital Hybridization

1. In a C=C bond:

A. Hybridization occurs between the s-orbital and one p-orbital

B. Hybridization occurs between the s-orbital and two p-orbitals

C. Hybridization occurs between the s-orbital and three p-orbital

D. Hybridization occurs between the s- and one p-orbitals

2. π bonds are formed by which of the following orbitals?

A. Two p-orbitals

B. Two s-orbitals

C. One s- and one p-orbital

D. All of the above

3. How would one best describe the orbitals required to form a π bond?

A. Parallel overlap of two s-orbitals

B. Overlap of one s- and one p-orbital

C. Perpendicular overlap of two p-orbitals

D. Parallel overlap of two p-orbitals

4. How would one best describe the orbital required to form a σ bond? Select all that apply.

A. Overlap of two s-orbitals

B. Overlap of one s- and one p-orbital

C. Overlap of two p-orbitals

D. Parallel overlap of two p-orbitals



Quiz 1.5 – Resonance Structures

1. Draw resonance contributors for each molecule below. Do not include structures that

are so unstable that their contributions are negligible. For each molecule’s set of resonance

contributors, indicate which is the greatest resonance contributor.



Quiz 1.5 – Resonance Structures (Continued)

2. Which of the following structures represents a correct resonance structure for molecule

A?

3. Draw resonance contributors for each radical molecule below. For each set of resonance

contributors, indicate which is the greatest resonance contributor.



Quiz 1.6 – Newman Projections

1. Which of the following represents the most stable Newman projection looking down the

C2–C3 bond of 2-methylbutane?

2. Which of the following represents the most stable Newman projection looking down the

C3–C2 bond of 2-methylbutane?

3. Which of the following represents the most stable conformation of 3,3-dimethylpentane

viewed along the C3-C4 bond?



Quiz 1.7 – Cycloalkanes and Ring Strain

1. Draw trans-1,2-dibromocyclohexane in a chair conformation.

2. Draw trans-1,2-dibromocyclohexane in its most stable chair conformation.

3. Which of the following represents the most stable chair conformation of the molecule

shown in the box below?

Ch. 2 – Acids and Bases DAT Organic Chemistry Outline


Quiz 2.1 – Acid-Base Definitions

1. The conjugate base of H3O+ is:

A. H3O–

B. H2O

C. H3O

D. H3O+

E. HO–

2. What is the conjugate acid of C6H5NH2?

A. C6H5NH3+

B. C6H5NH–

C. C6H5NH4+

D. C6H5NH2–

3. Which of the following is NOT a conjugate acid-base pair?

A. H2O, H3O+

B. Cl–, HCl

C. SO42–, HSO4

–

D. NO3–, HNO3

E. –OH, O2–

4. Identify each substance in the following reactions as an acid, a base, a conjugate base, or

a conjugate acid.

NH3 (aq) + HF (aq) → F– (aq) + NH4

+ (aq)

NaOH (aq) + H2O (l) → NaOH (aq) + H2O

(l)

KOH (aq) + H2CO3 (aq) → KHCO3 (aq) + H2O (l)

C2H3O2H (aq) + NaHCO3 (aq) → NaC2H3O2 (aq) + H2CO3 (aq)



Quiz 2.2 – Conjugate Base-Acid Relationship and pH Scale

1. Which of the following is the weakest acid?

A. H2S (KA = 1.1 × 10-7)

B. HCO2H (KA = 1.8 × 10-4)

C. HF (KA = 6.8 × 10-4)

D. NH4+ (KA = 5.6 × 10-10)

E. Acetic acid (KA = 1.8 × 10-5)

2. Which of the following molecules would be the strongest acid?

3. Which of the following molecules would be the strongest acid?

4. Of the acids shown in the table below, __________ is the strongest acid.

A. C2H3OH

B. H2C2O4

C. HClO2

D. HCO2H

E. H2C6H6O6

Continue to next page…

OHOH O



Quiz 2.2 – Conjugate Base-Acid Relationship and pH Scale (Continued)

5. Given the KA values in the table, which of the conjugate bases below is the strongest

base?

A. C2H3O–

B. HC2O4–

C. ClO2–

D. HCO2–

E. HC6H6O6–

6. If H2O has a pKA of 15.7 and acetic acid has a pKA of 4.75, which is a stronger base,

hydroxide (OH–) or acetate (C2H3O2–)?

7. Given the KB values in the table, which of the conjugate acids below is the weakest acid?

A. HCO2–

B. C5H5NH+

C. NH4+

D. H3NOH+

E. H2S



Quiz 2.3 – Ranking Acids and Bases with CARDIO (Charge)

1. Which of the red-colored H atoms below would be the most acidic?



4. Which of the red-colored H atoms below would be the most acidic? Which would be the

least?



Quiz 2.4 – Ranking Acids and Bases with CARDIO (Atom)

1. Which of the following is the strongest acid?

A. SeH2

B. GeH4

C. HBr

D. AsH3

2. Which of the following would be the strongest acid? Which would be the weakest?

A. H2Se

B. H2O

C. H2Te

D. H2S

3. Which of the following is the strongest acid? Which is the weakest?

A. HF

B. HBr

C. H2O

D. H2Se

4. Which of the following is the weakest acid?

A. HCl

B. H2O

C. H3N

D. H2Se

5. Which of the following is the most acidic?

A. H2O

B. CH4

C. H2S

D. H2Se

6. Which of the following is the most basic?

A. H3C–

B. CH4

C. NH3

D. OH–



Quiz 2.5 – Ranking Acids and Bases with CARDIO (Resonance)

1. Which of the following molecules is most acidic? Why?

2. Which of the red-colored hydrogen atoms in the molecules below is most acidic? Why?

3. Which of the labeled hydrogen atoms in the following structure is the most acidic?





Quiz 2.5 – Ranking Acids and Bases with CARDIO (Resonance) (Continued)


6. The pKA of acetone is about 20. The pKA of propane is about 50. Why?

7. Which of the red-colored alpha-hydrogen atoms is the LEAST acidic?

8. Sort the compounds below in order of increasing acidity of their alpha-hydrogen atoms

(colored red), from LEAST to MOST acidic:



Quiz 2.6 – Ranking Acids and Bases with CARDIO (Dipole Induction)

1. Sort the following molecules from least to most acidic.

2. Sort the following molecules from least to most acidic.

3. Which of the following will be least acidic? Which will be the most acidic?




Quiz 2.6 – Ranking Acids and Bases with CARDIO (Dipole Induction) (Continued)

4. Which of the following pairs does NOT correctly describe their relative acidities?

5. Sort the following molecules from least to most basic.

6. Which of the following would be a stronger base? Why?

7. Sort the following molecules from least to most basic.

8. Sort the following molecules from least to most nucleophilic.



Quiz 2.7 – Ranking Acids and Bases with CARDIO (Orbitals)

1. Which of the red-colored hydrogen atoms below is most acidic?

2. Which of the red-colored hydrogen atoms below is most acidic? Which is the least?





Quiz 2.8 – Acid and Base Review

1. Which of the options below is the conjugate acid of Molecule A?

2. Which of the following compounds is most acidic?




Quiz 2.8 – Acid and Base Review (Continued)

3. Which of the indicated hydrogen atoms is most acidic?

4. Which of the following compounds is most acidic?

Ch. 3 – Nomenclature DAT Organic Chemistry Outline


Quiz 3.1 – IUPAC Basics and Naming Alkanes

1. Please give the IUPAC name for the following structures:



Quiz 3.2 – Naming Cycloalkanes and Alkyl Halides

1. Give the names for each of the following structures:



Quiz 3.3 – Naming Alkenes

1. Name the following alkenes, including cis or trans designation:

2. Assign E or Z to the following compounds:

3. Name the following alkenes, including their correct E/Z designation:




Quiz 3.3 – Naming Alkenes (Continued)

4. Give the IUPAC names for the following compounds:

5. Which of these structures represents a trans (E) isomer?




Quiz 3.3 – Naming Alkenes (Continued)

6. What is the IUPAC name for this compound:

7. Give the IUPAC name for the following structures:



Quiz 3.4 – Naming Alcohols, Ethers, and Amines




Quiz 3.5 – Naming Aldehydes and Ketones




Quiz 3.6 – Naming Carboxylic Acids and Derivatives




Quiz 3.7 – Naming Aromatics




Quiz 3.8 – Naming Polyfunctional Compounds


2. Which of the following are considered terminal functional groups?

A. Ketones

B. Carboxylic acids

C. Aldehydes

D. Both B and C

3. The IUPAC name for the structure shown below ends with what suffix?

A. -ol

B. -ide

C. -al

D. -oic acid



Quiz 3.9 – Naming Spiro and Bicyclic Alkanes

1. Please provide a correct IUPAC name for each of the following spiro alkanes:

2. Please provide a correct IUPAC name for each of the following bicyclic alkanes:

Ch. 4 – Stereochemistry DAT Organic Chemistry Outline


Quiz 4.1 – Isomers

1. Are the following molecules isomers of each other? If so, what kind?




Quiz 4.1 – Isomers (Continued)

2. What are the following molecules?

A. Structural isomers

B. Enantiomers

C. Diastereomers

D. Identical compounds

E. Meso compounds



Quiz 4.2 – Chiral Centers

1. Please assign the correct R,S configuration to each of the following molecules:

2. Are each of the pairs of molecules shown below pairs of enantiomers?

3. Please assign the correct R,S configuration

to each stereocenter in the following molecule:

CH CH2

CCH3CH2

H

CH3

CH2CH3CH3

Br

H

HBr

CH2CH3CH3

Br

H

HBr

Please assign the correct IUPAC

name to the following molecule,

including the R,S designation.



Quiz 4.3 – Diastereomers

1.

2.

3.



Quiz 4.4 – Counting Stereoisomers

1. How many possible stereoisomers are there in the following molecule?

2. How many possible stereoisomers are there in the following molecule?



Quiz 4.5 – Chirality and Physical Properties

1. Which of the following statements is true about a pair of enantiomers?

A. They rotate plane-polarized light by exactly the same amount and in opposite

directions.

B. They rotate plane-polarized by differing amounts and in opposite directions.

C. They rotate plane-polarized light by differing amounts and in the same direction.

D. They have different melting points.

E. They have the same melting point, but different boiling points.

2. Which of the following could be separated by physical means?

A. Enantiomers

B. Racemic mixtures

C. Diastereomers

D. Meso compounds

E. None of the above

3. A 50/50 mixture two enantiomers is:

A. Called a racemic mixture

B. Optically inactive

C. Meso

D. Both A and B

E. None of the above

4.



Quiz 4.6 – Meso Compounds

1.

Quiz 4.7 – Fischer Projections

1. The molecule pictured in the box below is shown as a Fischer projection. Which of the

following tetrahedral structures represents the same molecule?




Quiz 4.7 – Fischer Projections (Continued)

2. Alanine, the amino acid pictured in the box below, is shown as a Fischer projection.

Which of the following tetrahedral structures represents the same molecule?

3. Threose, the four-carbon sugar pictured in the box below, is shown as a Fischer

projection. Which of the following line-bond structures represents the same molecule?



Quiz 4.8 – D vs. L Sugars

1. Categorize each of the following as D or L molecules:

2. Is S-valine, shown below, a “D” or an “L” amino acid?

Ch. 5 – Spectroscopy DAT Organic Chemistry Outline


Quiz 5.1 – IR Spectroscopy

1. IR spectroscopy is most useful for identifying:

A. The stereochemistry of molecules

B. A compound’s functional group

C. Enantiomeric excess in a non-racemic mixture

D. A compound’s purity

2. H2 doesn’t give an IR spectrum because:

A. It isn’t possible to get an IR spectrum of a gas

B. It has no atomic motions

C. H2 doesn’t have a net dipole moment

D. None of the above

3. The IR spectrum of an organic compound has no strong absorptions from 1600 to 2600

or any above 3000. What functional group is it likely to contain?

A. Alcohol

B. Aldehyde

C. Amine

D. ether

4. A strong infrared (IR) absorption band between 1750 and 1700 indicates which of the

following functional groups?

5. Which of the following would give a strong IR absorption band at 1720 cm-1?



Quiz 5.2 – UV Vis and Mass Spectrometry

1. UV spectroscopy is most useful for detecting:

A. Cumulated dienes

B. Carboxylic acids and amides

C. Conjugated alkenes

D. Esters

2. In mass spectrometry, peak abundances are measured relative to the:

A. M peak

B. Parent peak

C. Smallest peak

D. Largest peak

3. Mass spectrometry separates fragments according to:

A. mass

B. mass-to-charge ratio

C. size

D. shape

4. Which of these compounds would

most likely show a base peak at m/z = 43?

5. The key fragment at m/z = 45

corresponds which of the following

fragments?

6. A compound is analyzed by mass spectrometry.

Its base peak at m/z = 81 comes from the most

stable fragment. Which of the following is it?



Quiz 5.3 – Degrees of Unsaturation

1. How many degrees of unsaturation does the following formula have: C3H6O?

2. How many degrees of unsaturation does the following formula have: C2H6O2?





Quiz 5.4 – 13C-NMR Spectroscopy

1. How many different kinds of carbon atoms are there in the following molecules?

2. For each pair below, which of the two pink-colored carbon atoms in each pair is more

positively charged (and hence, will appear further to the left by NMR)?

3. Predict what the 13C-NMR spectrum should look like for each of the following molecules:



Quiz 5.5 – 1H-NMR Spectroscopy

1. How many different kinds of hydrogen atoms are there in the following molecules?

2. For each pair below, which of the sets of pink-colored hydrogen atoms in each pair is

more positively-charged (and hence, will appear further to the left by NMR)?

3. Predict what the 1H-NMR spectrum should look like for each of the following molecules.



Quiz 5.6 – Spectroscopy Analysis

*Note: You likely will not see anything this hard on the DAT, but if you can answer these

questions, you’ll be ready to answer anything spectroscopy related on the DAT.

1. Identify the compound that gives the following spectra. (Formula: C6H12O)

2. Identify the compound that gives the following spectra. (Formula: C6H12O2)

Continue on next page…



Quiz 5.6 – Spectroscopy Analysis (Continued)

3. Identify the compound that gives the following spectra. (Formula: C5H12O)

Ch. 6 – IM Forces and Lab Techniques DAT Organic Chemistry Outline


Quiz 6.1 – Intermolecular Forces

1. Can acetaldehyde (shown below) hydrogen-bond? What if we add water?

2. What types of intermolecular forces does testosterone have?

3. Which pair of elements would form a bond with the greatest ionic character?

A. B and Cl

B. C and P

C. Al and P

D. Li and Cl

E. N and F

4. Which of the following interactions gives ionic compounds their relatively high melting

points?

A. Hydrogen bonding

B. London forces

C. Ion-dipole forces

D. Ion-ion attraction

E. Dipole-dipole forces

5. Which of the following molecules will exhibit intermolecular hydrogen-bonding?

H

O

CH3

CH3

H

H

O

H

O H



Quiz 6.2 – Effect of IM Forces on Physical Properties

1. The following compounds all have similar molecular weights. Which compound would

have the LOWEST boiling point?


have the LOWEST boiling point?

3. Which of the following would have the HIGHEST boiling point?




Quiz 6.2 – Effect of IM Forces on Physical Properties (Continued)

4. Which is the following is TRUE?

A. As vapor pressure decreases, boiling point decreases.

B. As vapor pressure increases, boiling point increases.

C. As vapor pressure increases, boiling point decreases.

D. Vapor pressure increases with increasing molecular weight.

E. Boiling point increases with decreasing molecular weight.


have the LOWEST melting point?


have the LOWEST melting point?



Quiz 6.3 – Melting Points and Extractions

1. If partitioned (separated) between ether and water, which of the following molecules

would show the greatest preference for the water layer?

Quiz 6.4 – Acid-Base Extractions

1. Which of the following would be the best way to separate a carboxylic acid from an

amine?

A. Extract the carboxylic acid into aqueous HCl

B. Extract the amine into water

C. Extract the carboxylic acid into aqueous NaOH

D. Extract the carboxylic acid into water

E. Extract the amine into aqueous NaOH

2. Which of the following would be the best way to separate a phenol from an amine?

A. Extract the phenol into aqueous HCl

B. Extract the amine into water

C. Extract the phenol into water

D. Extract the amine into aqueous NaOH

E. Extract the phenol into aqueous NaOH

3. Which of the following would be the best way to separate a phenol from an amine?

A. Extract the amine into water

B. Extract the phenol into water

C. Extract the amine into aqueous HCl

D. Extract the amine into aqueous NaOH

E. Extract the phenol into ether



Quiz 6.5 – Distillation and Recrystallization

1. Which of the following is frequently used to separate volatile liquids with large

differences in their boiling temperatures?

A. Thin-layer chromatography

B. Gas-liquid chromatography

C. Sublimation

D. Distillation

E. Fractional distillation

2. Which of the following is frequently used to separate volatile liquids with moderate

differences in their boiling temperatures?



C. Sublimation

D. Distillation


3. Which of the following is sometimes used to purify volatile solids?



C. Sublimation

D. Distillation


4. Which of the following is sometimes used to purify non-volatile solids?



C. Sublimation

D. Distillation

E. Recrystallization



Quiz 6.6 – Chromatography

1. Which of the following can be used to separate non-volatile substances?

A. Sublimation

B. Distillation

C. Gas-liquid chromatography

D. Fractional distillation

E. Thin-layer chromatography

2. Which of the following methods would MOST effectively separate two volatile

compounds?

A. Silica gel chromatography

B. Thin layer chromatography

C. Extraction

D. Crystallization

E. Gas-liquid chromatography

Ch. 7 – Alkenes and Alkynes DAT Organic Chemistry Outline


Quiz 7.1 – Alkene Additions and Hydrohalogenations

1. Which is the most stable carbocation?

2. Which of the following is an intermediate in the Markovnikov addition of HBr to 1-

methylcyclohexene?

3. What is the major product of the following reaction?




Quiz 7.1 – Alkene Additions and Hydrohalogenations (Continued)


Quiz 7.2 – Carbocation Rearrangements

1. Draw the major organic product generated by the following reaction:

2. What is the major product of the Markovknikov addition of HBr to the following

molecule?



Quiz 7.3 – How to add –OH and –OR to Alkenes

1. Which of the following would produce a secondary alcohol when reacted with

oxymercuration-demercuration conditions?

2. Which best describes the regioselectivity and stereospecificity in the oxymercuration-

demercuration of an alkene?

A. Markovnikov orientation with syn-addition

B. Markovnikov orientation with anti-addition

C. anti-Markovnikov orientation with syn-addition

D. anti-Markovnikov orientation with anti-addition

E. Markonikov orientation with both syn- and anti-addition

3. Which of the following reactions will lead to the formation of methoxycyclopentane as

the major product?




Quiz 7.3 – How to add –OH and –OR to Alkenes (Continued)

4. Which set of reagents will accomplish the following transformation?

A. BH3-THF, then H2O2/NaOH

B. OsO4, t-BuOOH

C. H3O+/CH3OH

D. Hg(OAc)2/H2O, then NaBH4

E. m-CPBA, then NaOCH3




Quiz 7.4 – Adding Halogens to Alkenes

1. What are the major products of the following reactions?



4. Challenge Question: Draw the product(s) of the following reaction:



Quiz 7.5 – Anti-Markovnikov Alkene Additions

1. Predict the major organic product of the following reaction:

2. What compound is the expected product upon hydrohalogenation of

2-methylpent-2-ene with peroxide and HBr?

3. What is the major organic product of the following reaction?



Quiz 7.6 – Epoxides and Dihydroxylations


A. 1. H2O2 2. CH3OH

B. 1. (CH3)2S=CH2 2. CH3O–Na+

C. 1. Hg(OAc)2/NaOH, H2O2 2. CH3Li

D. 1. OsO4 2. CH3MgBr

E. 1. mCPBA 2. CH3MgBr


3. Predict the major product of the following reaction:




Quiz 7.6 – Epoxides and Dihydroxylations (Continued)

4. What reaction sequence is required to yield the product below?

A. II → IV → III

B. II → I

C. IV → III

D. III → IV

E. II → IV → I

5. Which starting material gives the product in the reaction sequence below?



Quiz 7.7 – Ozonolysis

1. Please identify the missing reactant:

2. What is the structure of a compound, which has a molecular formula of C6H10, which

upon ozonolysis and subsequent treatment with zinc and water, gives the following

product?




Quiz 7.7 – Ozonolysis (Continued)

3. What is the major organic product of the following reaction?

4. What is/are the product(s) of the following reaction?



Quiz 7.8 – Catalytic Hydrogenation

1. What are the products of the following reactions?

2. Which set of reagents will accomplish the following chemical transformation?

A. (1) NaNH2, (2) CH3Br, (3) H3O+

B. H2, Lindlar

C. Li, NH3

D. (1) LiAlH4, (2) H3O+

E. HgSO4, H2SO4

3. Which reagent is best for preparing (Z)-4-methyl-2-hexene from 4-methyl-2-hexyne?

A. H2, Pd/C

B. Na/NH3

C. H2NNH2, NaOH

D. Zn(Hg) / HCl

E. H2, Lindlar’s catalyst (Pd/CaCO3)



Quiz 7.9 – Alkyne Addition Reactions

1. Predict the products of the following reactions:




Quiz 7.10 – Alkyne Hydration and Alkylation



Ch. 8 – Substitution and Elimination Reactions DAT Organic Chemistry Outline


Quiz 8.1 – Substitution Reactions (Part 1)

1. In an SN2 reaction, what happens if you double the amount of the nucleophile or the

electrophile?

A. The rate will halve

B. The rate will stay the same

C. The rate will double

D. The rate will triple

E. The rate will quadruple

2. In an SN2 reaction, what happens if you double the amount of solvent?

A. The rate will halve

B. The rate will stay the same

C. The rate will double

D. The rate will triple

E. The rate will be 1/4th

5. Which of the following is a feature of SN2 reactions?

A. Their rate law is first-order

B. They produce a stereochemical inversion of configuration.

C. They have no rate-determining step.

D. Solvent concentrations do not affect outcome.

E. Steric factors do not influence the rate.

6. Which of the following will most readily undergo an SN2 reaction with NaOH?



Quiz 8.1 – Substitution Reactions (Part 2)

1. Determine if each of the following substitution reactions will happen by an SN1 or SN2

mechanism. Then predict the products:


Br

Li-I?

?

Br NaCN

?

Br

NaO

O

?ClHS-



Quiz 8.1 – Substitution Reactions (Part 2 Continued)

2. Determine if each of the following substitution reactions will happen by an SN1 or SN2


?

I

NaCN

Br

?NaO

O

OTsH2O

?heat

ClNaOH

?

?

I

NaO

O

?

OH

HO

O



Quiz 8.2 – Elimination Reactions

1. Determine if each of the following substitution reactions will happen by an E1 or E2


2. Predict the major products of each of the following E2 reactions:




Quiz 8.2 – Elimination Reactions (Continued)

3. Predict the major products of each of the following E1 reactions:

4. Predict the major products of each of the following elimination reactions:



Quiz 8.3 – How to Choose between SN1, SN2, E1, E2

1. Predict the major products of the following reactions and identify them as SN1, SN2, E1,

or E2:


CH3

Br

KOH

CH3

Br

CH3OH, heat

CH3

Cl

CH3

NaOH

CH3

OTs

CH3

CH3

H2O, heat

CH3

Br

CH3

CH3

OH

CH3

CH3

CH3

CH3

CH3

CH3

Br

NaO CH3

O

CH3

I

CH3

CH3

LiO

CH3

CH3

CH3



Quiz 8.3 – How to Choose between SN1, SN2, E1, E2 (Continued)

2. Predict the major products of the following reactions and identify them as SN1, SN2, E1,

or E2:

NaCN

CH3

CH3

I

Ch. 9 – Free Radical Halogenation and Diels Alder DAT Organic Chemistry Outline


Quiz 9.1 – Free Radical Halogenation

1. Show the major product(s) formed by reacting each of the following with Br2 and hv.

2. Which of the following is an example of a free radical termination step?

3. Which of the following reactions represents a propagation step in the free radical

bromination of propane?

CH3

CH3

CH3

CH3CH3

CH3

CH3CH3

CH3

CH3

CH3CH3

CH3

CH3

CH3

CH3

CH3



Quiz 9.2 – NBS in Radical Halogenation

1. What will be the major product(s) of the reaction of 1-methylcyclohexene with EACH of

the following reagents?

1. NBS/heat/peroxide

2. Br2/CH2Cl2

3. HBr

4. HBr/peroxide

Quiz 9.3 – Diels-Alder Reaction

1. Identify the diene and dienophile needed to assemble the following product by a Diels-

Alder reaction:

2. All of the following dienes would react in a Diels-Alder reaction EXCEPT for one. Which

one is the EXCEPTION?




Quiz 9.3 – Diels-Alder Reaction (Continued)

3. What is the major organic product of the following reaction sequence?

4. What is the major product expected of the following Diels–Alder reaction? (Note: (+/–)

refers to a racemic mixture)

Ch. 10 – Aromatic Compounds DAT Organic Chemistry Outline


Quiz 10.1 – How to Determine Aromaticity

1. Identify each of the following compounds as aromatic, non-aromatic, or anti-aromatic:

Quiz 10.2 – Effects of Aromaticity

1. Which of the following molecules will undergo an SN1 reaction more quickly? Why?

2. Which of the following molecules will be more acidic and why?



Quiz 10.3 – Side Reactions of Benzenes


2 . Predict the products of the following reactions:




Quiz 10.3 – Side Reactions of Benzenes (Continued)

3. What is the final product of the following reaction?

4. What is the final product of the following reaction?



Quiz 10.4 – Electrophilic Aromatic Substitution (EAS)

1. What are the products of the following reactions?

2. The reaction of this molecule with Cl2 and AlCl3 will form:




Quiz 10.4 – Electrophilic Aromatic Substitution (EAS) (Continued)

3. What is/are the product(s) of the following reaction?

Quiz 10.5 – Diazonium Salts

1. What are the products of each of the following reaction sequences?

Ch. 11 – Alcohols, Ethers, Epoxides DAT Organic Chemistry Outline


Quiz 11.1 – Substitution and Elimination of Alcohols

1. Which best describes the mechanism of the reaction pictured?

A. Free radical halogenation

B. SN1

C. SN2

D. E1

E. E2

2. Which set of reagents will accomplish the following transformation in the highest yield?

A. 1. PBr3 2. PhO–Na+

B. 1. NaI 2. Benzyl alcohol

C. 1. NaH 2. Benzene

D. 1. H3O+ 2. PhOH

E. 1. H3O+ 2. PhMgBr

3. Rank the following leaving groups in increasing order of reactivity (i.e., from worst to

best).

A. IV < I < III < V < II

B. II < V < III < I < IV

C. I < IV < III < II < V

D. V < IV < I < III < II

E. IV < III < I < II < V

4. What is the most likely mechanism by which this reaction occurs?

A. SN1

B. SN2

C. E1

D. E2



Quiz 11.1 – Substitution and Elimination of Alcohols (Continued)

5. Draw the mechanism and identify the major product of each reaction below:

Quiz 11.2 – Oxidizing Alcohols





Quiz 11.2 – Oxidizing Alcohols (Continued)



4. Using multistep synthesis, how could you convert the following starting material into the

indicated product?




Quiz 11.3 – Reactions of Ethers

1. What products would be formed by heating the following ethers with one equivalent of

HCl?

2. What products would be formed by heating the following ethers with excess HCl?

Quiz 11.4 – Reactions of Epoxides

1. Draw the product(s) of the following reaction sequence:



1. Cl2, H

2O

2. HO-

HCl

O

CH3OH

CH3O-

O

CH3OH



Quiz 11.4 – Reactions of Epoxides (Continued)

3. What reaction sequence is required to yield the product below?

A. II → IV → III

B. II → I

C. IV → III

D. III → IV

E. II → IV → I

4. Predict the major product of the following reaction:

Ch. 12 – Aldehydes and Ketones DAT Organic Chemistry Outline


Quiz 12.1 – Alcohol Reactions with Carbonyls

1. Identify the product and draw the reaction mechanism for the following transformation:

2. What are the organic products of the following reaction?

3. What product would you obtain if you reacted cyclohexanone with H+ and CH3CH2OH?

4. What product would you obtain if you reacted butanal with H+ and CH3OH?

5. How could you convert the reactant here into the product shown?

6. How could you convert the reactant here into the product shown?

CH3

O

acid

OH

OH

?



Quiz 12.2 – Amine Reactions with Carbonyls

1. What is the product of the following reaction?

2. What is the product of the following reaction?

3. What is the product of the following reaction sequence?



Quiz 12.3 – Hydride Reductions


2. How might you prepare the following alcohols from an aldehyde or ketone?

Quiz 12.4 – Grignards and Organolithium Reactions with Carbonyls



OH

H CH2CH2OHOH



Quiz 12.4 – Grignards and Organolithium Reactions with Carbonyls (Continued)

2. Which of the following compounds gives a secondary alcohol upon reaction with

methylmagnesium bromide, followed by acid workup?

A. butyl formate

B. 2-butanone

C. butanal

D. methyl butanoate

E. cyclopentanone

3. Use a Grignard reaction on an aldehyde or ketone to synthesize the following

compounds:

A. butan-2-ol

B. 1-phenylpropan-2-ol

C. 1-methylcyclohexanol

D. diphenylethanol


A. cold dilute KMnO4, then PhCH2Br

B. PDC, CH2Cl2, then PhOH

C. Hg(OAc)2/NaOH, H2O2, then PhLi

D. OsO4, then PhMgBr

E. O3/(CH3)2S, then PhMgBr

Quiz 12.5 – Wittig Reaction

1. Identify the missing reagent:

A. Ph3P+—CH2

–

B. CH2I2, Zn(Cu)

C. 1. CH3MgBr; 2. H2O

D. CH2=CH2, Ru catalyst


O

?

CH2



Quiz 12.5 – Wittig Reaction (Continued)


Quiz 12.6 – Michael Additions (1,4-Addition)

1. Predict the major organic product of the following reaction.

2. The following compound was prepared by a conjugate addition reaction between an

α,β -unsaturated ketone and an alcohol. Identify the two reactants:

O O

H3C

Ch. 13 – Carboxylic Acids and Acid Derivatives DAT Organic Chemistry Outline


Quiz 13.1 – Interconversion of Acid Derivatives

1. Which of the following reagents would accomplish the following transformation in

highest yield?

2. Why doesn’t this reaction work?




Quiz 13.2 – Physical Properties of Carboxylic Acids

1. How would you prepare each of the following products, starting from a Grignard

reagent?

Quiz 13.3 – Fischer Esterification and Saponification


2. What is the major organic product of the

following reaction?



Quiz 13.4 – Hydride Reductions of Acid Derivatives

1. Which of the following compounds provides butane-1,4-diol as one of the products when

reacted with LiAlH4 in anhydrous diethyl ether?

A. I only

B. II only

C. III only

D. I and II

E. I and III



A. liq. NH3

B. NaBH4, CH3OH

C. PCC, CH2Cl2

D. LiAlH4, Et2O

E. H2NNH2




Quiz 13.4 – Hydride Reductions of Acid Derivatives (Continued)

4. All of the following statements regarding organometallic compounds are correct EXCEPT

for one. Which one is the EXCEPTION?

A. Grignard reagents add to the carbonyl group of aldehydes and ketones.

B. Grignard reagents are decomposed in protic solvents.

C. A Grignard reagent reacts as a negatively charged carbanion.

D. Alkyllithium and Grignard reagents do not add to esters.

E. Grignard reagents can be prepared in ether or tetrahydrofuran.



Quiz 13.5 – Mild Hydride Reductions

1. Which of the following compounds is hydrolyzed most slowly with OH–?





Ch. 14 – Alpha Substitution Reactions of Carbonyls DAT Organic Chemistry Outline


Quiz 14.1 – Alpha Substitution Reactions

1. Rank the indicated hydrogen atoms from LEAST acidic to MOST acidic.

A. A < B < C

B. C < B < A

C. C < A < B

D. B < C < A

E. B < A < C

2. Which statement regarding the following equilibrium is true?

A. II is the conjugate base of III.

B. Equilibrium favors I and II.

C. I is 3 times more acidic than IV.

D. I and III are resonance structures.

E. II is the strongest base in this equilibrium system.





Quiz 14.2 – Alpha Halogenation and Haloform Reaction

1. What is/are the major product(s) of the following reaction?

2. Show how you could convert each of the following starting materials into the products

indicated:




Quiz 14.2 – Alpha Halogenation and Haloform Reaction (Continued)

3. 2-Acetylcyclohexanone is treated with excess D2O in catalytic base. How many deuterium

atoms are expected to be exchanged with hydrogen atoms in this molecule?

A. 2

B. 7

C. 3

D. 5

E. 6

4. Assuming that complete deuteration occurs, how many deuterium (D) atoms are

incorporated into the following molecule?

A. 3

B. 4

C. 5

D. 6

E. 7



Quiz 14.3 – Aldol Condensation

1. Which of the following compounds is the product of an Aldol addition reaction?

2. Predict the major organic product of the following reaction:

3. Show how to form the following products from an aldehyde or ketone, using an aldol

condensation:

A. 2-methyl-3-hydroxypentanal

B. 4,5-diethyl-5-hydroxy-3-octanone



Quiz 14.4 – Claisen Condensation

1. Give the product of the following Claisen condensation reaction:

2. Give the product of the following Claisen condensation reaction:

3. Identify the starting material(s) and reaction conditions used to form the indicated

product through a Claisen condenation:

4. Which of the following molecules would decarboxylate when heated? Why?



Quiz 14.5 – Acetoacetic Ester Synthesis

1. How could you convert the given starting material into the product indicated?

2. How could you perform each of the following conversions?

A. ethyl acetate --> butan-2-one

B. propanoic acid --> pentan-3-one

Quiz 14.6 – Malonic Ester Synthesis



hybridization bond angle hybridization?outlines/… · ch. 1 – bonding, resonance, and molecular...

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