Organic Chemistry : Organic Functional Groups and Molecules

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #31 : Organic Functional Groups And Molecules

What is the IUPAC name for the following compound?

Screen shot 2016 02 17 at 7.32.56 pm

Possible Answers:

Correct answer:

Explanation:

The molecule is an amide (a molecule of the form ). The parent chain is the unbroken chain containing the carbonyl () group, including the carbonyl carbon. Thus, in the molecule shown, the parent chain consists of four carbons with no double/triple bonds (giving the root ""). The most important functional group is the amide group, so the suffix to the molecule's name is  (thus ""). Furthermore, the carbon chain automatically labels the carbonyl carbon as carbon number  so there is no need to label the amide functional group with a locand (it's redundant information). Alkyl groups attached to the amide nitrogen are given the locand "" to show that they're on the nitrogen. Thus, the molecule is called .

Example Question #191 : Organic Chemistry

Name this compound according to IUPAC naming conventions:

Screen shot 2016 02 17 at 12.49.23 pm

Possible Answers:

4-ethyl-octan-2-one

5-ethyloctan-2-one

5-ethyloctanal

5-propylheptan-2-one

5-propylheptanal

Correct answer:

5-ethyloctan-2-one

Explanation:

When naming an organic compound by the IUPAC, it's best to first start by identifying the functional groups present.

In this particular case we have:

A ketone here:

 Screen shot 2016 02 17 at 1.01.17 pm

and an ethyl group in the middle:

 Scomeon

Next, we should identify what functional group has the highest priority, as that will form the base name of the compound:

According to IUPAC convention, Carboxylic Acids and their derivatives have the highest priority then carbonyls (ketones in this case) then alcohols, amines, alkenes, alkynes, and alkanes, so in this case the ketone group has the highest priority and therefore makes up the name of the base compound.

Next, we want to number the longest carbon chain with the highest priority functional group with the lowest number. In this case this means we want the ketone to be carbon number #2, which is the lowest number it can possibly be so let's start there and number the carbon chain.

You should get something like this:

Screenshot

 

Now that we have numbered the carbon chain we can begin our naming.

Let's start with the base name:

According to IUPAC convention the base name for a ketone compound is -one, so in this case we have a octan-2-one.

We also have an ethyl group at carbon five. This gives us 5-ethyloctan-2-one, which is our final answer.

 

Now let's look at the wrong answer choices:

1) 5-propylheptan-2-one is wrong because the longest carbon chain has 8 carbons and following the path of the ethyl group as part of the main chain prevents naming being done for the longest possible carbon chain.

2) 5-ethyloctanal is incorrect because it mistakes the ketone for an aldehyde as the suffix -al refers to aldehydes which are RCHOs that can only be carbon 1.

3) 5-propylheptanal is wrong because the longest carbon chain is 8 carbons long, not 7, and this compound isn't an aldehyde.

4) 4-ethyl-octan-2-one is wrong because the ethyl is at carbon 5 and not carbon 4.

Example Question #31 : Organic Functional Groups And Molecules

What is the IUPAC name for the compound shown?

Screen shot 2016 02 17 at 7.33.19 pm

Possible Answers:

Correct answer:

Explanation:

This molecule is an ester (a molecule of the form . The parent chain is the unbroken chain containing the carbonyl () group, including the carbonyl carbon. Thus, in the molecule shown, the parent chain consists of four carbons with no double/triple bonds (giving the root ""). The most important functional group is the ester group, so the suffix to the molecule's name is obtained by dropping the "" suffix from the corresponding carboxylic acid and adding "." (thus ). Alkyl groups attached to the ester oxygen are placed before the ester functionality as a separate word.

Example Question #31 : Organic Functional Groups

What is the IUPAC name for the compound shown?

Screen shot 2016 02 17 at 7.34.00 pm

Possible Answers:

Correct answer:

Explanation:

This molecule is an ester (a molecule of the form . The parent chain is the unbroken chain containing the carbonyl () group, including the carbonyl carbon. Thus, in the molecule shown, the parent chain consists of four carbons with no double/triple bonds (giving the root ""). The most important functional group is the ester group, so the suffix to the molecule's name is obtained by dropping the "" suffix from the corresponding carboxylic acid and adding "." (thus ). The methyl substituent on the parent chain is on carbon number , because the starting carbon in the parent chain is the carbonyl carbon. 

Alkyl groups attached to the ester oxygen are placed before the ester functionality as a separate word.

Example Question #121 : Organic Concepts

What is the IUPAC name for the following compound?

Screen shot 2016 02 17 at 7.33.13 pm

Possible Answers:

Correct answer:

Explanation:

The longest carbon chain in the molecule has four carbons (thus "") and the lack of double bonds makes it an alkane (thus ""). The highest priority functional group is the carbonyl  group on the end of the chain. The molecule is thus classified as an "aldehyde" because the carbonyl is on the end, and the carbonyl carbon is automatically designated to be carbon number 1 in the chain. When naming aldehydes, they are given the suffix "", so the molecule is called "." Finally, the only other substituent that needs to be mentioned is the bromine on carbon number . Thus, the molecule is .

Example Question #31 : Organic Functional Groups And Molecules

What is the IUPAC name for the compound shown?

Screen shot 2016 02 17 at 7.33.55 pm

Possible Answers:

Correct answer:

Explanation:

The molecule shown is an acyl chloride, which is a carboxylic acid derivative. It is named by taking the corresponding carboxylic acid, removing the "" suffix from its IUPAC name, and adding "."

The corresponding carboxylic acid will be the molecule without the chlorine and in its place is a hydroxyl group. This is a carboxylic acid that contains three carbons with no double/triple bonds (Thus ""). Carboxylic acids are named by adding the suffix "" after the parent chain. Thus, the carboxylic acid is called "."

So, taking the name of the corresponding carboxylic acid, removing the "" suffix from its IUPAC name, and adding "" yields "."

Example Question #191 : Organic Chemistry

Name this compound according to IUPAC convention:

Screen1

Possible Answers:

3,6-diethylcyclopentanal

2,4-diethylcyclopentanecarbaldehyde

3,6-diethylcyclopentanecarbaldehyde

2,4-diethylpentanal

2,4-diethylcyclopentanal

Correct answer:

2,4-diethylcyclopentanecarbaldehyde

Explanation:

When naming an organic compound by the IUPAC, it's best to first start by identifying the functional groups present.

An aldehyde as shown here:

Screen3

And two ethyl substituents as shown here:

Screen2Screen4

 

 

Next, we should identify what functional group has the highest priority, as that will form the base name of the compound:

 

According to IUPAC convention, Carboxylic Acids and their derivatives have the highest priority then carbonyls (in this case the aldehyde) then alcohols, amines, alkenes, alkynes, and alkanes, so in this case the aldehyde group has the highest priority and therefore makes up the name of the base compound.

 

Next, we want to number the longest carbon chain with the highest priority functional group with the lowest number. In this case this means we want the carbon on the ring attached to the aldehyde to be carbon number #1, so let's start there and number the carbon chain around the ring.

 

You should get something like this:

 Screen81128

Now that we have numbered the carbon chain we can begin our naming.

Let's start with the base name:

According to IUPAC convention when we have an aldehyde attached to the ring normally (in this case cyclopentane) and put carbaldehyde after it, so in this case the base name is cyclopentanecarbaldehyde.

Next we wish to number ring such that the ethyl substituents have the lowest numbers possible, this is done by making ethyl group next to carbon #1, the second carbon (2-ethyl), then the second ethyl group is 4-ethyl.

 

Since there are two ethyls the substituents are 2,4-diethyl, so the final name of the compound is 2,4-diethylcyclopentanecarbaldehyde.

 

Now let's go over the wrong answers:

1) 2,4-diethylcyclopentanal is incorrect because according to IUPAC naming conventions we name the ring normally (cyclopentane) and then put carbaldehyde after its normal name.

2) 2,4-diethylpentanal is incorrect because this compound is a ring and not a straight chain.

3) 3,6-diethylcyclopentanecarbaldehyde is incorrect because the substituents can have lower numbers by making the ethyl group next to the first carbon, 2-ethyl.

4) 3,6-diethylcyclopentanal is wrong because the substituents can have lower numbers by making the ethyl group next to the first carbon, 2-ethyl. Also according to IUPAC naming conventions we name the ring normally (cyclopentane) and then put carbaldehyde after its normal name.

Example Question #1 : Identifying Amino Compounds

Ephedrine (shown below) contains what type of amine?

Mcat_problem_set_1

Possible Answers:

Neutral

Tertiary

Primary

Secondary

Quaternary

Correct answer:

Secondary

Explanation:

A secondary amine is an amine (nitrogen atom) that is attached to two carbon-containing groups (alkyl groups or aryl groups). The nitrogen in ephedrine is attached to two alkyl groups, making it a secondary amine.

Primary amines are generally written as . Secondary amines are generally written as . A tertiary amine will be bound to three different R-groups. Quaternary amines require a positive charge on the nitrogen atom to accommodate a fourth R-group.

Example Question #31 : Organic Functional Groups And Molecules

The amino functional group in the given molecule is best described as a __________.

Q9

Possible Answers:

Achiral tertiary amine

Chiral tertiary amine

Chiral secondary amine

Achiral secondary amine

Chiral tertriary amine

Correct answer:

Chiral tertiary amine

Explanation:

An amino group is a nitrogen-containing functional group, and is the part pictured on the right of the given molecule. This amine has three substituents: the alkyl ketone, the methyl, and the ethyl. Hydrogens do not count as "substituents." Any amine with three substituents is considered a "tertiary" amine.

This amine is chiral because it has four different substitutions at the nitrogen atom, which is the definition of chirality. 

Note: "tetriary" is not a real term in organic chemistry.

 

Example Question #31 : Organic Functional Groups

Which of these is a tertiary amine?

Possible Answers:

Aniline

Trimethylamine

None of the other answers

Piperidine

Ammonia

Correct answer:

Trimethylamine

Explanation:

A tertiary amine has three organic groups bonded to it. Triethylamine has three ethyl groups bonded to it, so that is the correct answer. Ammonia is so it has no organic groups attached. Piperidine is a six-membered ring with a nitrogen as one of the members, making it a secondary amine. Aniline is a benzene ring with a  bonded to it, so it is a primary amine.

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