GRE Subject Test: Chemistry : GRE Subject Test: Chemistry

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

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Example Questions

Example Question #1 : Hydrocarbons

Which of the following can reduce an alkene to an alkane?

Possible Answers:

Lithium aluminum hydride (LiAlH4)

H2/Pd and H2/Raney nickel

H2/Raney nickel

Lithium aluminum hydride (LiAlH4) and H2/Pd

H2/Pd

Correct answer:

H2/Pd and H2/Raney nickel

Explanation:

Neither lithium aluminum hydride, nor sodium borohydride will reduce C–C double bonds.

H2/Raney nickel and H2/Pd can each (individually) reduce an alkene to an alkane. Since both H2/Raney nickel and H2/Pd can reduce the alkene, the answer is both of those reagents. This is a catalytic hydrogenation reaction, and H2/Raney nickel not only reduces C–C double bonds, but also carbonyl compounds.

Example Question #2 : Functional Group Reactions

Identify the major organic product expected from the acid-catalyzed dehydration of 2-methyl-2-pentanol.

Possible Answers:

cis-3-methyl-2-pentene

2-methyl-2-pentene

None of the other answers

2-methyl-1-pentene

3-methyl-1-pentene

Correct answer:

2-methyl-2-pentene

Explanation:

The initial compound is a five-carbon alkane chain with methyl and hydroxy groups on the second carbon. Dehydration involves the hydrogenation of the hydroxy group. That group then leaves, and a double bond is formed. Zaitsev's rule states that double bonds are more stable on more highly substituted carbons. The double bond forms across carbons two and three.

Example Question #3 : Functional Group Reactions

Untitled

What is the IUPAC name of the given diene?

Possible Answers:

3-chloro-2,5-dimethyl-2,6-heptadiene

None of these answers

5-chloro-3,6-dimethyl-1,5-heptadiene

5-chloro-3,5-dimethyl-1,6-heptadiene

3-chloro-2,5-dimethyl-1,5-heptadiene

Correct answer:

5-chloro-3,6-dimethyl-1,5-heptadiene

Explanation:

You must begin counting the carbons so that the first functional substituent has the lowest possible number. In this case, C1 is connected to C2 by the double bond, meaning we start counting from the left.

The longest carbon chain is seven carbons so the parent molecule is heptane. With this numbering, there are methyl groups on carbons 3 and 6 and a chlorine on carbon 5.

Substituents are named in alphabetical order and two double bonds result in a diene. Thus, the correct answer is 5-chloro-3,6-dimethyl-1,5-heptadiene.

Example Question #1 : Help With Alkene Reactions

The stereochemical pathway for the hydrogenation of an alkene with a metal catalyst, such as platinum, occurs via __________.

Possible Answers:

syn addition

formation of a bridged carbocation

Markovnikov addition

anti-Markovnikov addition

anti addition

Correct answer:

syn addition

Explanation:

Hydrogenation of an alkene with a metal catalyst, such as platinum, occurs via syn addition.

It is important to note the three main types of reactions for alkenes. The first type of reaction is a 2-step mechanism in which the electrophile attacks the carbocation nucleophile. This can yield syn or anti products. The second type of reaction is a 2-step mechanism that forms a bridged carbocation as the intermediate. This can yield only anti products. The third and last type of reaction is a 1-step addition. This can only yield syn products.

An example of the third type of reaction is the addition of a hydrogen with palladium, platinum, or nickel as demonstrated in the picture.

1

Example Question #171 : Gre Subject Test: Chemistry

What is(are) the product(s) in the Pd-catalyzed hydrogenation if 1,2-dimethylcyclopentene?

Possible Answers:

1,1-dimethylcyclopentene

A mixture of trans- and cis-1,2-dimethylcyclopentane

Trans-1,2-dimethylcyclopentane

Dimethylcyclopentane

Cis-1,2-dimethylcyclopentane

Correct answer:

Cis-1,2-dimethylcyclopentane

Explanation:

The product for this hydrogenation is cis-1,2-dimethylcyclopentane.

It is important to note the three main types of reactions for alkenes. The first type of reaction is a 2-step mechanism in which the electrophile attacks the carbocation nucleophile. This can yield syn or anti products. The second type of reaction is a 2-step mechanism that forms a bridged carbocation as the intermediate. This can yield only anti products. The third and last type of reaction is a 1-step addition. This can only yield syn products.

The cis product alone forms because the reagents used were hydrogen and a metal catalyst palladium (other common metal catalysts are platinum and nickel). This type of reagent with an alkene will always be a 1-step addition that yields solely syn products. Cis-1,2-dimethylcyclopentane is the only answer that solely indicates syn products.

Example Question #1 : Organic Chemistry

Nbs

What reagent will complete this reaction?

Possible Answers:

SOBr2

N-bromosuccinimide (NBS) / light

PBr3

None of these

Br2 / light

Correct answer:

N-bromosuccinimide (NBS) / light

Explanation:

N-bromosuccinimide (NBS) brominates at allylic positions. Br2 will not complete this reaction with the presence of the double bond. 

Example Question #2 : Functional Group Reactions

What is the best reagent for abstracting a hydrogen from ethyne?

Possible Answers:

None of these

Correct answer:

Explanation:

The triple bond in ethyne makes the hydrogens slightly more acidic than those found in ethane. A very strong base, such as the conjugate base of ammonia, would be able to abstract that hydrogen. The abstraction turns the base into ammonia. It also creates a carbanion that can be used for chain extension and alkyne synthesis.

Example Question #4 : Functional Group Reactions

Untitled

What is the product of the compound when it reacts with two equivalents of base?

Possible Answers:

1-pentene

1-pentyne

None of these

2-pentyne

2-pentene

Correct answer:

2-pentyne

Explanation:

For each equivalent of base, a pi bond is formed between the carbons initially bound to the bromine atoms. For each bond formed, a bromine leaving group leaves the hydrocarbon. One equivalent of base abstracts a hydrogen. The electrons from the bond to the hydrogen create a pi bond. This occurs twice, and a triple bond is formed. The result is a 5-carbon chain with a triple bond between the second and third carbons. This molecule is 2-pentyne.

Example Question #172 : Gre Subject Test: Chemistry

Starting with an alkyne, synthesis of a cis alkene is driven upon addition of which of the following reagents?

Possible Answers:

Correct answer:

Explanation:

Reduction of an alkyne with hydrogen and Lindlar's catalyst will result in a cis alkene. While  is a reducing agent, when added to an alkyne, a trans alkene is formed. Potassium permanganate is an oxidizing agent and thus will not reduce the triple bond. The Grignard reagent is used to add organic substituents onto carbonyls. Addition of one equivalent of chlorine in carbon tetrachloride solvent yields a trans alkene; addition of a second equivalent of chlorine yields a tetrachloro alkane.

Example Question #1 : Lipids

Which of the following molecule is a type of terpene?

Possible Answers:

 because it is derived from a pentene

 because it is derived from a pentene

 because it is derived from an isoprene

 because it is derived from an isoprene

Correct answer:

 because it is derived from an isoprene

Explanation:

Terpenes are special classes of lipids that are derived from isoprene units. An isoprene unit’s molecular formula is ; therefore, terpenes must contain a molecular formula that is derived from a empirical formula.

The molecular formula consists of seven isoprene units ( = ); therefore,  is a type of terpene.

Pentene is an alkene with the molecular formula .  () is derived from pentene units; however, terpenes do not have pentene units.

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