Organic Chemistry : Identifying Other Organic Compounds

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

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Example Question #161 : Organic Concepts

Name this compound according to IUPAC conventions:

 Screen1

Possible Answers:

4-ethyl-2-hydroxycyclopentonyl chloride

4-ethyl-2-hydroxypentonyl chloride

3-ethyl-5-hydroxypentonyl chloride

4-ethyl-2-hydroxycyclopentanecarbonyl chloride

3-ethyl-5-hydroxycyclopentonyl chloride

Correct answer:

4-ethyl-2-hydroxycyclopentanecarbonyl chloride

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:

 

An acyl chloride:

Screen2 

An Alcohol (hydroxy) group:

Screen3

 

and an Ethyl group:

 Screen4

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 Acid derivatives including acyl halides have the highest priority then carbonyls then alcohols, amines, alkenes, alkynes, and alkanes, so in this case the Ester 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 acyl chloride to be carbon number #1, so let's start there and number the carbon chain.

 

You should get something like this:

 Screen5

 

Let's start with the base name:

According to IUPAC convention the base name for an acyl halide ring requires us to name the ring normally and then put carbonyl ____ide (where ___ is the name of the halogen) after it. In this case the base name becomes cyclopentanecarbonyl chloride.

Next we must try to make the next greatest priority group the lowest priority, which is the alcohol (hydroxy) group, and since this is next to carbon #1 it becomes carbon #2.

This means our name thus far for the compound is 2-hydroxycyclopentanecarbonyl chloride.

 

Finally we have an ethyl group at carbon #4, so it becomes 4-ethyl. Now we order our substituents named in alphabetical order so the final name is 4-ethyl-2-hydroxycyclopentanecarbonyl chloride.


Now let's look at the wrong answer choices:

1) 4-ethyl-2-hydroxycyclopentonyl chloride is wrong because according to IUPAC nomenclature cyclic acyl halides must be named normally with carbonyl ___ide (where ___ is the name of the halide) at the end of the name of the ring.

2) 4-ethyl-2-hydroxypentonyl chloride is wrong because the base name used is for the straight chain version of the compound when this compound is a ring.

3) 3-ethyl-5-hydroxypentonyl chloride is name because the hydroxy group is a higher priority than the ethyl substituent, so it needs to have a lower number if possible according to IUPAC rules. It is also wrong because the base name used is for the straight chain version of the compound when this compound is a ring.

4) 3-ethyl-5-hydroxycyclopentonyl chloride is wrong because the hydroxy group is a higher priority than the ethyl substituent, so it needs to have a lower number if possible according to IUPAC rules. It is also wrong because according to IUPAC nomenclature cyclic acyl halides must be named normally with carbonyl ___ide (where ___ is the name of the halide) at the end of the name of the ring.

Example Question #71 : Organic Functional Groups

Name this compound according to IUPAC conventions:

Screen81

Possible Answers:

5-hydroxy-6-oxohexanoic acid

3-hydroxy-2-oxocyclohexanecarboxylic acid

5-hydroxy-6-oxocyclohexanecarboxylic acid

3-hydroxy-2-oxohexanoic acid

3-hydroxy-2-oxocyclohexanoic acid

Correct answer:

3-hydroxy-2-oxocyclohexanecarboxylic acid

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 Carboxylic Acid:

 Screen82

A Ketone:

 

Screen83

An Alcohol (hydroxy) group:

 

Screen84 

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 Acid and their derivatives have the highest priority then carbonyls then alcohols, amines, alkenes, alkynes, and alkanes, so in this case the Carboxylic acid 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 carboxylic acid to be carbon number #1, so let's start there and number the carbon chain.

You should get something like this:

Screen85 

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 an carboxylic acid ring requires us to name the ring normally and then put carboxylic acid after it. In this case the base name becomes cyclohexanecarboxylic acid.

The next highest priority group is the ketone next to the carbon #1, which is named as a substituent as it is lower priority than the carboxylic acid, so we have 2-oxocyclohexanecarboxylic acid.

Finally we have a hydroxy group at carbon 3, which is 3-hydroxy, so after ordering the substituents alphabetically we get the final answer of 3-hydroxy-2-oxocyclohexanecarboxylic acid.

Now let’s look at the wrong answers:

1) 3-hydroxy-2-oxocyclohexanoic acid is wrong because according to IUPAC nomenclature cyclic acids must be named normally with carboxylic acid at the end of the name of the ring.

2) 3-hydroxy-2-oxohexanoic acid is wrong because this is a ring, and that is the name given to the straight chain version of this compound.

3) 5-hydroxy-6-oxocyclohexanecarboxylic acid is wrong because it ignores the fact that the ketone group is a higher priority substituent than the alcohol, so it can be assigned to be on carbon 2 instead of 6.

4) 5-hydroxy-6-oxohexanoic acid is wrong because this is a ring, and that is the name given to the straight chain version of this compound. It is also wrong it ignores the fact that the ketone group is a higher priority substituent than the alcohol, so it can be assigned to be on carbon 2 instead of 6.

Example Question #71 : Organic Functional Groups

Name this compound according to IUPAC naming conventions:

Screen91

Possible Answers:

4-amino-3-hydroxypentenoyl chloride

4-amino-3-hydroxypentanoyl chloride

4-amino-3-hydroxybutanoyl chloride

2-amino-3-hydroxypentan-5-oyl chloride

4-amino-3-hydroxyhexanoyl chloride

Correct answer:

4-amino-3-hydroxypentanoyl chloride

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:

An acyl chloride:

Screen92

An alcohol:

Screen93

and An amine:

Screen94

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 Acid derivatives including acyl halides (in the case the acyl chloride) have the highest priority then carbonyls then alcohols, amines, alkenes, alkynes, and alkanes, so in this case the acyl chloride 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 carbonyl carbon on the acyl chloride to be carbon number #1 as it has the highest priority, so let's start there and number the carbon chain.

 

You should get something like this:

Let's start with the base name:

 Screen95

According to IUPAC naming conventions for straight chained acyl halides their names end with -oyl __halide (where __ is the name of the halide), so in this case we have -oyl chloride. Since this is a five carbon chain we have pentanoyl chloride as our base name.

 

Next, notice the next highest priority group is an alcohol substituent (hydroxy) group on carbon #3, so we have 3-hydroxypentanoyl chloride.

Finally we have an amine on carbon #4, so we name this substituent 4-amino, so after ordering the substituents alphabetically we get the final answer: 4-amino-3-hydroxypentanoyl chloride.

 

Now let’s look at the wrong answers:

1) 4-amino-3-hydroxypentenoyl chloride is wrong because it says pentenoyl instead of pentanoyl. Pentenoyl implies there is an alkene present and there isn't.

2) 2-amino-3-hydroxypentan-5-oyl chloride is wrong because it makes the amino group a higher priority and therefore lower number than the alcohol and acyl halide, when naming must be done according to the acyl halide as it is the highest priority group.

3) 4-amino-3-hydroxyhexanoyl chloride is wrong because it miscounts the number of carbons on the longest chain, which is 5, not 6.

4) 4-amino-3-hydroxybutanoyl chloride is wrong because it miscounts the number of carbons on the longest chain, which is 5, not 4.

Example Question #241 : Organic Chemistry

Name this compound according to IUPAC naming conventions:

Screen101

Possible Answers:

2-methyl-3-methoxypentan-5-oic acid

4-methoxy-3-methylpentanoic acid

2-methoxy-3-methylpentan-5-oic acid

1-hydroxy-4-methoxy-3-methylpentanone

 

3-methyl-4-methoxypentanoic acid

Correct answer:

4-methoxy-3-methylpentanoic acid

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 carboxylic acid:

Screen102

A methyl group:

 

Screen103

and a methoxy ether group:

Screen104

 

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 then alcohols, amines, alkenes, alkynes, and alkanes, so in this case the Carboxylic acid 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 carbonyl carbon on the carboxylic acid to be carbon number #1 as it has the highest priority, so let's start there and number the carbon chain.

 

You should get something like this:

 

Screen105

 

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 an carboxylic acid requires us to name the chain and then put __oic acid after it. In this case the base name becomes pentanoic acid.

Our next highest priority group is the ether (methoxy group), which is labeled as 4-methoxy and since the methyl group is directly between the methoxy and carboxylic acid group it becomes labeled as 3-methyl, as that is the only way to allow the carboxylic acid to be carbon #1.

 

Finally after ordering the substituents alphabetically we get the final answer of 4-methoxy-3-methylpentanoic acid

 which is our final answer. 

Now let’s look at the wrong answers:

1) 3-methyl-4-methoxypentanoic acid is wrong because according to IUPAC naming conventions the substituents must be organized in alphabetical order therefore 4-methoxy should be listed before 3-methyl in the name.

2) 2-methoxy-3-methylpentan-5-oic acid is wrong because the carboxylic acid, which is the highest priority should be assigned the lowest number, which is 1, not 5.

3) 2-methyl-3-methoxypentan-5-oic acid is wrong because because the carboxylic acid, which is the highest priority should be assigned the lowest number, which is 1, not 5. It is also wrong because according to IUPAC naming conventions the substituents must be organized in alphabetical order therefore 3-methoxy should be listed before 2-methyl in the name.

4) 1-hydroxy-4-methoxy-3-methylpentanone is wrong because it mistakes the carboxylic acid group as being an alcohol and a ketone and names them independently.

Example Question #31 : Identifying Other Organic Compounds

Name this compound according to IUPAC naming conventions:

Screen111

Possible Answers:

2,2,2-tribromo-4-hydroxyhexanamide

6,6,6,-tribromo-4-hydroxyheptan-7-amide

2,2,2-tribromo-4-hydroxyheptanamide

4-hydroxy-6,6,6,-tribromoheptan-7-amide

4-hydroxy-2,2,2-tribromoheptanamide

Correct answer:

2,2,2-tribromo-4-hydroxyheptanamide

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:

 

An Amide:

Screen112

 

3 Bromine (bromo) groups:

 

Screen113

An Alcohol (Hydroxy) group:

Screen114

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 Acid derivatives including amides have the highest priority then carbonyls then alcohols, amines, alkenes, alkynes, and alkanes, so in this case the amide 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 carbonyl carbon on the acyl chloride to be carbon number #1 as it has the highest priority, so let's start there and number the carbon chain.

 

You should get something like this:


Screen115 


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 an amide requires us to name the chain and then put __amide after it. In this case the base name becomes heptanamide.

We also have 3 bromo groups at carbon 2 which gives us 2,2,2-tribromoheptanamide.

 


Finally we have a hydroxy group at carbon 4, so after ordering the substituents alphabetically we get the final answer of 2,2,2-tribromo-4-hydroxyheptanamide.

Now let’s look at the wrong answers:

1) 4-hydroxy-2,2,2-tribromoheptanamide is wrong because according to IUPAC naming conventions the substituents in the name must be named alphabetical order and since B comes before H, 2,2,2-tribromo goes before 4-hydroxy in the name.

2) 6,6,6,-tribromo-4-hydroxyheptan-7-amide is wrong because according to IUPAC naming conventions the highest priority group should have the lowest number, so in this case the amide should be on carbon #1 and have a lower number than the hydroxy group.

3) 4-hydroxy-6,6,6,-tribromoheptan-7-amide is wrong because according to IUPAC naming conventions the highest priority group should have the lowest number, so in this case the amide should be on carbon #1 and have a lower number than the hydroxy group. It is also wrong because according to IUPAC naming conventions the substituents in the name must be named alphabetical order and since B comes before H, bromo goes before hydroxy in the name.

4) 2,2,2-tribromo-4-hydroxyhexanamide is wrong because the longest carbon chain is 7 carbons long, not 6.

Example Question #71 : Organic Functional Groups

Name this compound according to IUPAC naming conventions:

Screen121

Possible Answers:

2-hydroxy-3-iodo-3-phenylpropanamide

3-Benzyl-2-hydroxy-3-iodopropanamide

2-hydroxy-1-iodo-1-phenylpropan-3-amide

2-hydroxy-3-iodo-3-Benzylpropanamide

1-iodo-1-phenyl-2-hydroxypropan-3-amide

Correct answer:

2-hydroxy-3-iodo-3-phenylpropanamide

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:

 

An amide group:

Screen122

An alcohol (hydroxy) group:

Screen123

An iodine (Iodo) group:

Screen124

and A phenyl group:

Screen125

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 Acid derivatives including amides have the highest priority then carbonyls then alcohols, amines, alkenes (this priority is shared with phenyl groups), alkynes, and alkanes, so in this case the amide 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 carbonyl carbon on the amide to be carbon number #1 as it has the highest priority, so let's start there and number the carbon chain.

 

You should get something like this:

Screen126

 

 

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 an amide requires us to name the chain and then put amide after it. In this case the base name becomes propanamide.

Next since there is only one way to number this with the amide being on carbon #1, the hydroxy group is on carbon. This gives us 2-hydroxypropanamide.

 

Finally, on carbon #3 we have two substituents: An iodo group and a benzene group. The IUPAC name for a benzene group substituent is phenyl, so now let's order the substituents alphabetically to get our final name of the compound, which is 2-hydroxy-3-iodo-3-phenylpropanamide.

Now let’s look at the wrong answers:

1) 2-hydroxy-3-iodo-3-Benzylpropanamide is wrong because Benzyl is the common name of a benzene substituent, not the IUPAC name. The IUPAC name is phenyl. It is also wrong because the substituents aren't organized alphabetically in the compound name.

2) 3-Benzyl-2-hydroxy-3-iodopropanamide is wrong because Benzyl is the common name of a benzene substituent, not the IUPAC name. The IUPAC name is phenyl.

3) 2-hydroxy-1-iodo-1-phenylpropan-3-amide is wrong because according to IUPAC rules the highest priority group, which is the amide, should have the lowest number on the carbon chain available, which is carbon #1 not 3.

4) 1-iodo-1-phenyl-2-hydroxypropan-3-amide is wrong because according to IUPAC rules the highest priority group, which is the amide, should have the lowest number on the carbon chain available, which is carbon #1 not 3. It is also wrong because the substituents aren't organized alphabetically in the compound name.

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