GRE Subject Test: Chemistry : Organic Chemistry

Study concepts, example questions & explanations for GRE Subject Test: Chemistry

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Example Questions

Example Question #41 : Organic Chemistry

Which substance is used as a reducing agent?

Possible Answers:

Correct answer:

Explanation:

A reducing agent is a substance that readily donates an electron to another substance. They consist primarily of elements with low electronegativities such as hydrogen. Therefore, the answer is  (sodium borohydride) which consists primarily of hydrogen atoms.

Example Question #1 : Carbocations

What intermediate is involved in the conversion of compound B to compound C?

Mcat_1

Possible Answers:

Tertiary carbocation

Tertiary carbanion

Secondary radical

Secondary carbocation

Tertiary radical

Correct answer:

Tertiary carbocation

Explanation:

The strong sulfuric acid protonates the hydroxyl group of compound B, resulting in the loss of water as a leaving group and the generation of a carbocation intermediate. Since this carbocation carbon is attached to three other carbons, this is a tertiary carbocation. It is bound to the phenyl substituent, a methyl group, and the branched carbon chain.

Example Question #241 : Organic Chemistry

Which of the following carbocation intermediates requires the least activation energy?

Possible Answers:

Carbo3

Carbo2

Carbo1

Carbo4

Cannot be determined

Correct answer:

Carbo1

Explanation:

The more stable the carbocation, the lower the activation energy for reaching that intermediate will be. The more substituted a carbocation is, the more stable it is. The carbocation bonded to three alkanes (tertiary carbocation) is the most stable, and thus the correct answer.

Secondary carbocations will require more energy than tertiary, and primary carbocations will require the most energy.

Example Question #42 : Organic Chemistry

Carbon 1:

8

Carbon 2:

9

Let's say we react the given compound with . During the first step of the reaction, will the hydrogen be added to carbon 1 or carbon 2, why?

Possible Answers:

Carbon 2 because the bromine will first attack the double bond from the least sterically hindered side

Carbon 1 because the bromine anion is large and requires space to react

Carbon 2 because the intermediate will be a secondary carbocation

Carbon 1 because the intermediate will then be a secondary carbocation

Carbon 1 because the intermediate will be a primary carbocation

Correct answer:

Carbon 1 because the intermediate will then be a secondary carbocation

Explanation:

The correct answer is: carbon 1 because the intermediate will then be a secondary carbocation.

This is a case of  addition across a double bond where  stands for any halide. The first step in this reaction is the attack of  by the double bond. This will create two intermediates, the first being the halide anion  (so in our case ), the second being a carbocation on our compound at one of the two carbons that formerly shared the double bond. 

If the hydrogen attached the carbon 2 then we would have a positive charge on carbon 1 and vice versa. A positive charge on carbon 1 is known as a primary carbocation (a carbon attached to 1 other carbon or function group), which is rarely if ever seen due to its overwhelming instability. A positive charge on carbon 2 is known as a secondary carbocation (a carbon attached to 2 other carbons or functional groups) and is much more stable than a primary carbocation.

We would want the more thermodynamically stable intermediate for our reaction to proceed, so we would want the positive charge on carbon 2 and the hydrogen attached to carbon 1. 

Example Question #1 : Carbocations

4

 

If the carbon being pointed to was deprotonated (resulting in a positive charge on it). Would the resonance form (the positive charge being redistributed to the carbon with a bromine) be more stable than a secondary carbocation? Why? 

Possible Answers:

Yes because bromine donates some electrons

Yes because bromine is an electrophile

No because bromine is an electrophile

No because secondary carbocations are unstable

No because bromine's bulky electron cloud will interfere

Correct answer:

No because bromine is an electrophile

Explanation:

The resonance form of this compound would put the positive charge on the carbon attached to the bromine. Unfortunately this carbon is already slightly positive due to the electron withdrawing effects of bromine due to its high electrophilicity. So this resonance form would be more unstable than a secondary carbocation due to the increased concentration of positive charge from bromine's electron withdrawal. 

Example Question #211 : Gre Subject Test: Chemistry

Which of the following steps of free radical chlorination does not produce a free radical as a product?

Possible Answers:

Termination

Initiation

Propagation

Halogenation

Correct answer:

Termination

Explanation:

The three steps of a free radical chlorination reaction are, in order, initiation, propagation, and termination.

Free radicals are produced in the initiation and propagation steps. The termination steps combine any two free radicals formed in the reaction to produce a compound that has no unpaired electrons (free radicals).

Example Question #1 : Organic Intermediates

Which of the following transformations includes an enolate intermediate?

 Q12

Possible Answers:

I and III

I, II, and III

III only

I and II

II and III

Correct answer:

II and III

Explanation:

Enolates are formed by an oxygen anion bound to an alkene carbon. Reactions II and III include an enolate intermediate, as shown in the mechanisms below, whereas reaction I is a simple SN2 reaction and does not include an enolate intermediate. Enolates are highlighted in red. 

A12

Example Question #1 : Stereochemistry

The molecules shown below are best described as __________.

Molecules

Possible Answers:

diastereomers

isomers

epimers

enantiomers

Correct answer:

isomers

Explanation:

The molecules in this problem are isomers because they each have unique configurations and do not share the same funcitonal groups at the same carbon positions. Enantiomers are reflections of each other. Diastereomers are stereoisomers that differ at one or more stereocenters, while epimers are stereoisomers that differ at only one stereocenter.

Example Question #1 : Stereochemistry

Which of the following is not a geometric isomer of pentene?

Possible Answers:

Screen shot 2015 12 08 at 8.52.13 pm

Screen shot 2015 12 08 at 8.52.08 pm

Screen shot 2015 12 08 at 8.51.59 pm

All of these are geometric isomers of pentene.

Screen shot 2015 12 08 at 8.52.05 pm

Correct answer:

Screen shot 2015 12 08 at 8.52.13 pm

Explanation:

Geometric isomers are compounds that have the same molecular formula but they differ in the way they are arranged spatially. Pentene carries the molecular formula, . The longest chain of carbon atoms should be five carbons. According to its name, pentene is an alkene due to the -ene form its name, therefore must also contain a  bond. The only compound without a chain of 5 carbons consecutively is Screen shot 2015 12 08 at 8.52.13 pmand this compound is not a geometric isomer of pentene.

Example Question #14 : Isomerism And Stereoisomers

A molecule has three chiral centers. How many stereoisomers of this compound will have different boiling points compared to the original molecule?

Possible Answers:

Seven

Six

Two

One

Correct answer:

Six

Explanation:

The first step is to determine how many stereoisomers there are for this molecule. Since the number of stereoisomers is dependent on the number of chiral carbons, we can solve according to the equation , where  is the number of chiral centers. Since there are three chiral centers, we determine that there are eight stereoisomers for this molecule. Keep in mind that this number includes the original molecule.

Next, we need to compare the different stereoisomers to the original molecule. The original molecule will have one enantiomer and six diastereomers. Remember that enantiomers have the same physical properties, so we will not include this isomer in the final answer. Diastereomers, on the other hand, have different physical properties compared to the original molecule. As a result, six stereoisomers will have different boiling points compared to the original molecule.

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