Identifying Other Organic Compounds

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Organic Chemistry › Identifying Other Organic Compounds

Questions 1 - 10
1

What is the IUPAC name of the molecule shown?

Img 1324

Methylcyclohexane

Methylcycloheptane

1-Methylcyclohexane

1-Methylcycloheptane

Explanation

The molecule's longest carbon chain has 6 carbons (thus, "hex-"), and the lack of double bonds makes it an alkane (thus "hexane"). The longest chain is a ring structure (thus "cyclohexane"), and the one branching group is a carbon chain consisting of one carbon and no double bonds (a "methyl" group). Because there are no other functional groups on the molecule there is no need to put a number before the location of the methyl group (thus "methylcyclohexane").

2

What is the IUPAC name for the molecule shown?

Img 1325

3-Bromopentane

2-Bromopentane

3-Bromopropane

2-Bromopropane

Explanation

The molecule's longest carbon chain has 5 carbons (thus, "pent"), and the lack of double bonds makes it an alkane (thus "pentane"). The one functional group is a bromine atom attached to carbon number 3 (whether read from left to right or right to left, the bromine is always on carbon number 3). Thus, the molecule is named "3-bromopentane."

3

What is the IUPAC name for the following compound?

Screen shot 2016 02 17 at 7.32.49 pm

Explanation

The longest carbon chain is carbons long (thus ""), and the double bond makes it an alkene (thus ""). The highest priority functional group is the double bond, and the carbon chain must be numbered such that this functional group is given the lowest number carbon. Counting from left to right puts the double bond between carbons and , which is lower than counting from right to left , therefore the numbering goes from left to right, and the molecule is thus a "." The substituents are a bromine on carbon and a chlorine on carbon . IUPAC rules state that the substituents are listed in alphabetical order when naming (thus "").

Finally, stereochemistry must be taken into account. On carbon , the bromine is of higher priority than the methyl group (when taking atomic number into account, per the Cahn-Ingold-Prelog rules), and is located "above" the double bond. On carbon , the chlorine group is higher priority, and is located "below" the double bond. Because the higher priority groups are across the double bond from each other, the molecule is given the "E" designation.

4

Which of the following is an appropriate solvent for synthesizing Grignard reagents?

Explanation

Grignard reagents are very strong bases, and therefore can be spoiled by protons. Grignard reagents are so basic in fact that any protic solvent will render them useless. Dimethyl ether is the only non-protic solvent, and is therefore the correct answer.

5

Img 0600

What type of orbital is the lone pair on the nitrogen found in?

sp2

sp

sp3

p

Explanation

In this molecule, the carbon that is directly attached to the nitrogen and the nitrogen itself are sp2 hybridized. This means that, within this bond, there are three sp2 orbitals present and the lone pair on the nitrogen occupies one of them.

6

Img 0601

How many conjugated atoms are present in the given molecule?

Explanation

A conjugated molecule is one that has its atoms arranged in such a way that allows p orbitals to lie parallel to each other. This allows for electron delocalization, which ultimately provides increased stability for the molecule. To find conjugated atoms, look for alternating single and multiple bonds. The circled carbon atoms are the only ones that are conjugated in this molecule.

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7

What is the general formula of an ether?

Explanation

is the general formula of an ether.

8

What is the IUPAC name for the compound shown?

Img 1327

Cyclopentene

Cyclopentane

1-Cyclopentane

1-Cyclopentene

Explanation

The molecule's longest carbon chain has 5 carbons (thus, "pent"), and the one double bond makes it an alkENE (thus "pentene"). The longest chain is a ring structure (thus "cyclopentene"). Because the IUPAC rules automatically assign the location of the first double bond to carbons 1 and 2, there is no need for a number locand.

9

What is the IUPAC name for the following compound?

Screen shot 2016 02 17 at 7.33.04 pm

Explanation

The longest carbon chain is carbons long (thus ""), and the double bond makes it an alkene (thus ""). The highest priority functional group is the double bond, and the carbon chain must be numbered such that this functional group is given the lowest number carbon. Counting from either direction puts the double bond between carbons and the molecule is thus a "." The substituents are a bromine on carbon when counting from right to left, and from left to right. The carbon chain is numbered so substituents are given the lowest numbers possible. Thus, the carbon chain is numbered from right to left, and the molecule is .

Finally, stereochemistry must be taken into account. On carbon , the carbon chain is of higher priority than the implied hydrogen (when taking atomic number into account, per the Cahn-Ingold-Prelog rules), and is located "below_"_ the double bond. On carbon , the alkyl group is higher priority, and is located "above_"_ the double bond. Because the higher priority groups are across the double bond from each other, the molecule is given the "E" designation.

10

Name this compound according to IUPAC convention:

Screenshot1

3-bromo-5-chloro-4-fluorocyclohexanecarboxamide

3-bromo-5-chloro-4-fluorocyclohexanamide

3-bromo-5-chloro-4-fluorohexanamide

5-bromo-3-chloro-4-fluorocyclohexanecarboxamide

5-bromo-3-chloro-4-fluorocyclohexanamide

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 shown here:

Screenshot2

A Bromine (bromo) group shown here:

Screenshot5

A Fluorine (fluoro) group shown here:

Screenshot4

and A chlorine (chloro) group shown here:

Screenshot3

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 carbon on the ring that the amide is attached to to be #1, so let's start there and number the carbon chain, and then we go in alphabetical order for the substituents, so we make bromo a lower number than chloro.

You should get something like this:

Screenshot63812

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

Let's start with the base name:

Since this is a cyclic compound we name the compound cyclohexanecarboxamide, as in IUPAC nomenclature you name the ring normally then put carboxamide at the end to show it has an amide attached to it.

Next we number the substituent alkyl halides so that they are in alphabetically order and the one that is nearest to the beginning of the alphabet has the lowest priority, so we have a 3-bromo, 4-fluoro, and 5-chloro.

Putting this together and ordering the substituents named in alphabetical order, we get 3-bromo-5-chloro-4-fluorocyclohexanecarboxamide as our final answer.

Now let's go over the wrong answers:

  1. 3-bromo-5-chloro-4-fluorocyclohexanamide is wrong because in IUPAC nomenclature we must name the ring normally and then put carboxamide after it.

  2. 3-bromo-5-chloro-4-fluorohexanamide is wrong because it ignores the fact that this compound is cyclic (a ring), and would be the correct name if this were a straight chain compound.

  3. 5-bromo-3-chloro-4-fluorocyclohexanecarboxamide is wrong because the substituents aren't numbered in alphabetical order so that the lowest number alkyl halide is closest to the beginning of the alphabet.

  4. 5-bromo-3-chloro-4-fluorocyclohexanamide is wrong because the substituents aren't numbered in alphabetical order so that the lowest number alkyl halide is closest to the beginning of the alphabet. It is also wrong because in IUPAC nomenclature we must name the ring normally and then put carboxamide after it.

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