CHM 2210 Final Exam Review - · PDF fileCHM 2210 Final Exam Review ... What would be the major product of dehydrohalogenation of 2 ... How many mono-chlorination products are obtained

Spring 2016 CHM 2210 Study Union Review

CHM 2210 Final Exam Review

Direction: All questions have ONE correct answer and have been divided by topic. Please note that “D” stands

for deuterium which is an isotope of hydrogen. Deuterium is used as an isotopic label to track regio or stero

chemistry during a reaction. A decent number of the questions assume that you know this, and now you do.

Nomenclature

1. In the structure shown, the functional groups in the triangle, rectangle, pentagon and

circle (in this same order) are

A. Amine, ketone-ether, ether, amide

B. Amide, ester, ether, ketone-amine

C. Amine, ester, ether, amide

D. Amine, ester, ether, ketone-amine

2. What is the correct IUPAC name for this compound?

A. 1,1,1,6-tetramethylheptane

B. 1-tert-butyl-4-isopropylbutane

C. 2,2,7-trimethyloctane

D. 1-tert-butyl-4-isopropyloctane

3. What is the IUPAC name for this compound?

A. 1-methyl-4-ethyl-1-pentanol

B. 1,4-dimethyl-1-hexanol

C. 3-methyl-6-heptanol

D. 5-methyl-2-heptanol



A. ortho-bromocyclohexanol

B. endo-2-bromocyclohexanol

C. cis-2-bromocyclohexanol

D. trans-2-bromocyclohexanol


A. (E)-3,5-dimethyl-2-hexene

B. (Z)-3,5-dimethyl-2-hexene

C. (Z)-1,2-dimethyl-2-isobutylethylene

D. (E)-3,5,5-trimethyl-2-pentene


A. 1-tert-butyl-2-butanol

B. 5,5-dimethyl-3-hexanol

C. 2,2-dimethyl-4-hexanol

D. 1,1,1-trimethyl-3-pentanol


A. (Z)-5-ethyl-4-hexen-2-ol

B. (Z)-3-methyl-3-hepten-6-ol

C. (E)-5-methyl-4-heptne-2-ol

D. (Z)-5-methyl-4-hepten-2-ol


Structure, Hybridization and Resonance.

1. What are the respective hybridizations of the atoms numbered 1-4 in the compound

below?

A. sp2 sp sp2 sp3

B. sp2 sp2 sp3 sp

C. sp3 sp2 sp2 sp

D. sp3 sp2 sp3 sp

2. Which carbocation is the most stable?

A.

B.

C.

D.


3. What factor is responsible for a greater heat of combustion per CH2 for cyclopropane

than the heat of combustion per CH2 for cyclohexane?

A. Cyclohexane has a different hydrogen to carbon atom ratio than cyclopropane.

B. Cyclohexane is a strained ring relative to cyclopropane.

C. Cyclopropane is a strained ring relative to cyclohexane.

D. Cyclohexane has more carbon atoms than cyclopropane.

4. Onto which of the numbered atoms in this structure is the negative charge

delocalized?

A. 2, 4, 6 only

B. 1, 3, 5, 8 only

C. 1, 3, 5 only

D. 2, 4, 6, 7 only

5. Which carbocation is the most stable?

A.

B.

C.

D.


Stereoisomerism

1. Which is the most stable conformation for cis-1-bromo-3-methylcyclohexane?

A.

B.

C.

D.

2. Which molecule has the R configuration?

A. .

B. .

C. .

D. .


3. The absolute configuration of the two carbon atoms in this compound are

A. R- left carbon atom; R-right carbon atom

B. S- left carbon atom; S-right carbon atom

C. S- left carbon atom; R-right carbon atom

D. R- left carbon atom; S-right carbon atom

4. The configurations of the two stereocenters in this Fischer projection are?

A. 2R, 3R

B. 2R, 3S

C. 2S, 3R

D. 2S, 3S

5. The product of this reaction will be?

A. Achiral but not meso

B. A mixture of diastereomers

C. A meso compound

D. A racemate

6. Which statement is true?

A. Compounds with R stereocenters rotate plane-polarized light clockwise

B. For equal concentrations and equal path lengths, solutions of (+) and (-) enantiomers

rotate plane polarized light equally, but in opposite directions.

C. Racemic mixtures can rotate plan polarized light either clockwise or

counterclockwise

D. Meso compounds con rotate plane polarized light either clockwise or

counterclockwise

7. What is the relationship between these two structures?

A. Identical molecules

B. Conformational isomers

C. Constitutional isomers

D. Enantiomers

E. Diastereomers


8. Which of these molecules could have an enantiomers?

A. cis-1,3-cyclohexandiol

B. trans-1,2-cyclohexandiol

C. cis-1,4-cyclohexandiol

D. trans-1,4-cyclohexandiol

Substitution and Eliminations

1. What is the principle product of the reaction shown?

A. CH3OCC(CH3)3

B. CH3OCH3

C. CH2=C(CH3)2

D. CH3OCH2CH(CH3)2

2. What is the structure of the reactant that would yield the two products shown?

A. .

B. .

C. .

D. .


3. What is the expected major reaction pathway for the reaction shown?

A. E2

B. E1

C. SN2

D. SN1

4. What is the order of rates from fastest to slowest for the reaction of three

nucleophiles (methanol, sodium methoxide, or CH3NH2) with propyl bromide?

A. Methanol > CH3NH2 > methoxide

B. CH3NH2 > methoxide > methanol

C. Methoxide > CH3NH2 > methanol

D. Methoxide > methanol > CH3NH2

5. Which alkyl halide would you expect to undergo SN1 hydrolysis most rapidly?

A. (CH3)3CI

B. (CH3)3CBr

C. (CH3)3CCl

D. (CH3)3CF

6. Which of these anions would be the most nucleophilic towards methyl iodide in an

ethanol solution?

A. .

B. .

C. .

D. .


7. Which compound would react fastest in the SN2 reaction shown?

A. .

B. .

C. .

D. .

8. What is the major elimination product from the reaction shown?

A. .

B. .

C. .

D. .


9. What would be the major product of dehydrohalogenation of 2-cholorpentane by

potassium hydroxide?

A. 1-pentene

B. 2-pentene

C. 2-methyl-1-butene

D. 2-methyl-2-pentene

E. None of the above

10. Why would concentrated hydro bromic acid be an inappropriate catalyst for the

dehydration of alcohols?

A. HBr is too weakly acidic to protonate the alcohol

B. The conjugate base, Br-, is a good nucleophile and it would attack the carbocation to

form an alkyl bromide

C. HBr is strongly acidic, so the water molecule would not be a good leaving group

after the protonation of the alcohol.

D. HBr would be more likely to promote rearrangement of the carbocation

intermediate.

11. What would be the first step in the dehydration of cyclohexanol in sulfuric acid?

A. Loss of hydroxide

B. Loss of a proton by the alcohol

C. Formation of a sulfite ester

D. Protonation of the alcohol.

Radical Reactions

1. Which of the following will yield only one product when treated with N-

bromosuccinimide?

A. Cyclohexane

B. Butane

C. Methylcyclopentane

D. All of the above



2. Which of the following is a reasonable resonance structure for the intermediate

formed when 2, 2-dimethylcyclopentene is treated with N-bromosuccinimide?

A. .

B. .

C. .

D. All of the above


3. Which of the following radicals is the MOST stable?

A. .

B. .

C. .

D. .


4. How many mono-chlorination products are obtained when 2-methyl-pentane is reacted

with Cl2 and light? How many when reacted with N-bromosuccinimide?

A. Cl: 5, NBS:3

B. Cl: 1, NBS: 1

C. Cl: 5, NBS: 1

D. Cl: 5, NBS: 5

E. Cl: 1, NBS: 5

5. Which monomer below is commonly called isoprene and can act to yield the polymer

shown?

A. 2-methyl-1-butene

B. 2-methyl-2-butene

C. 3-methyl-1,2-butadiene

D. 2-methyl-1,3-butadiene


Alcohols and Phenols

1. Which of the following sequences of reagents could be used to convert 1-

methylcyclohexanol to 1-methylenecyclohexane.

A. A bulky base; such as tert-butoxide.

B. Tosylate (TsCl) in pyridinium followed by sodium ethoxide

C. Conc. Sulfuric acid.

D. Tosylate (TsCl) in pyridinium followed by tert-butoxide

E. Conc. Hydro bromic acid


2. Which of the following structures represents the product obtained after 3-

ethylcyclohexanol is treated with pyridinium chlorochromate in dichloromethane?

A.

B.

C.

D.


3. Which reagents would be best for converting 1-butanol into the structure shown below:

A. Sodium dichromate with sulfuric acid and water

B. Excess Lithium aluminum hydride followed by water

C. pyridinium chlorochromate in dichloromethane

D. All of the above


4. Which of the following will result in an optically active sample when (R)-2-butanol is

turned into (S)-2-bromobutane?

A. Hydro bromic acid

B. Tosylate (TsCl) in pyridinium followed by sodium bromide

C. Phosphorus tribromide

D. All of the above



5. Which of the following is the product after the reactant shown below reacts with

excess molecular hydrogen and a platinum catalyst?

A. 1,6-heptandiol

B. 2,7-heptandiol

C. 2-heptanol

D. Heptane


6. Which sequence of reagents could be used to convert the structure shown below into

3-bromohexane?

A. Sodium borohydride and methanol followed by phosphorous tribromide

B. Lithium aluminum hydride followed by water followed by hydro bromic acid

C. H2 and a nickel catalyst followed by Tosylate (TsCl) in pyridinium followed by sodium

bromide

D. All of the above


7. Which of the following compounds would poison a Grignard reagent?

A. 1-Heptanol

B. Tert-butyl methyl ether

C. Methyl ethyl ketone

D. All of the above



8. Which of the following compounds would poison a Grignard reagent?

A. Ethanol

B. Propanoic acid (3 carbon chain with carboxylic acid functional group)

C. 2-methyl-1,3-hexandiol

D. All of the above


Ethers, epoxides

1. Which set of products is expected from the reaction shown?

A. .

B. .

C. .

D. No reaction will occur


2. What is the product of the reaction shown?

A. .

B. .

C. .

D. .

3. Which reaction is best suited for the preparation of the ether shown?

A. .

B. .

C. .

D. .


4. Which reaction would produce phenyl propyl ether?

A. .

B. .

C. .

D. .

5. What is the major product of the reaction shown?

A. .

B. .

C. .

D. .


6. What is the expected product of the reaction shown?

A. .

B. .

C. .

D. .

Disclaimer: I do not see your final exams before you do, if at all! These questions are

based off the material in the course that tends to be difficult for students. Please do not

use this as your only source of studying. You should review all lecture material, any

chapters in the text you didn’t understand, your old exams and any other materials your

professor provided for you. Best of luck.

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CHM 2210 Final Exam Review - · PDF fileCHM 2210 Final Exam Review ... What would be the major product of dehydrohalogenation of 2 ... How many mono-chlorination products are obtained