Organic Chemistry : Assigning Ortho, Meta, Para

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #11 : Assigning Ortho, Meta, Para

What is the product of the reaction shown?

Screen shot 2015 12 26 at 9.13.10 pm

Possible Answers:

I only

I and III

III only

I, II, and III

Correct answer:

I and III

Explanation:

In the molecule shown, the aldehyde group will direct incoming substituents to positions meta to it, and both the the hydroxyl group AND the fluorine group will direct incoming substituents to positions ortho or para to them. Options I and III show the incoming substituent meta to the aldehyde group, as well as either ortho or para to both the fluorine group and hydroxyl group. Therefore, they are both possible products.

Note: because option III shows attachment at a carbon that is slightly less sterically hindered than that of option I, option III will be produced in a slightly greater quantity.

Example Question #12 : Assigning Ortho, Meta, Para

Predict the major product in the reaction shown.

Screen shot 2015 12 26 at 9.14.15 pm

Possible Answers:

II

I

III

IV

Correct answer:

III

Explanation:

The reagents shown will add a bromine to an aromatic ring through an electrophilic aromatic substitution mechanism. A nitro  group is a strong electron withdrawing group and a benzene deactivator. All benzene deactivators (with the exception of halogens) direct incoming substituents to the meta  positions. Therefore, option III is the major product.

Example Question #12 : Assigning Ortho, Meta, Para

What is a major product of the following reaction?

Screen shot 2015 12 26 at 9.14.35 pm

Possible Answers:

III only

I only

I and II

II only

Correct answer:

I only

Explanation:

This is an example of a Friedel-Crafts acylation reaction, which will add an acyl group (alkyl group containing a carbonyl () group) to a benzene ring at the carbonyl carbon (shown below).

Screen shot 2015 12 26 at 10.36.31 pm

This reaction proceeds using an electrophilic aromatic substitution reaction mechanism. The presence of the hydroxyl group on the benzene will affect where the incoming acyl group will attach. A hydroxyl group is a strong benzene activator, which will direct incoming substituents to positions ortho  or para  to it. Option I is the only option shown where the incoming substituent is attached at either the ortho or para position.

Example Question #13 : Assigning Ortho, Meta, Para

Predict the major product of the reaction shown.

Screen shot 2015 12 26 at 9.14.56 pm

Possible Answers:

I only

III only

II only

I and III

Correct answer:

III only

Explanation:

This reaction proceeds using an electrophilic aromatic substitution reaction mechanism. The presence of the amino group on the benzene will affect where the incoming acyl group will attach. An amino group is a strong benzene activator, which will direct incoming substituents to positions ortho  or para  to it. Option III is the only option shown where the incoming substituent is attached at either the ortho or para position on a benzene ring.

Example Question #361 : Organic Chemistry

If the molecule phenol (hydroxybenzene) were to undergo electrophilic aromatic substitution, which carbon(s) will the hydroxyl group direct incoming substituents to? (Start labeling carbons with number  being the carbon containing the hydroxyl group,  being the one immediately next to it, and continuing around the ring).

Possible Answers:

 only

, and 

 and 

, and 

Correct answer:

, and 

Explanation:

Several resonance structures can be drawn for the molecule phenol. These are shown below.

Screen shot 2015 12 26 at 9.15.15 pm

Because the overall charge distribution puts partial negative charges on carbons , and , these carbons have an increased nucleophilic character. Therefore, these carbons are more likely than the other carbons to accept an incoming electrophilic substituent, making these positions more likely to be substituted. Carbons  and  are known as the ortho positions, and carbon  is known as the para position.

Example Question #14 : Assigning Ortho, Meta, Para

If the molecule nitrobenzene were to undergo an electrophilic aromatic substitution, on which carbon(s) will the incoming substituent likely be directed to? (When numbering carbons on the benzene ring, label the carbon containing the nitro group as carbon number , the one immediately next to it as carbon number , and continue around the ring in that direction.

Possible Answers:

, and 

 and 

 and 

All carbons are equally likely to be substituted.

Correct answer:

 and 

Explanation:

Several resonance structures can be drawn for the molecule nitrobenzene. These are shown below.

Screen shot 2015 12 26 at 9.11.16 pm

From these resonance structures, an overall molecular electronic distribution can be determined:

Screen shot 2015 12 26 at 9.11.29 pm

Because the overall charge distribution puts partial positive charges on carbons , and , these carbons have an increased electrophilic character. Therefore, these carbons are less likely than the other carbons to accept an incoming electrophilic substituent, making these positions less likely to be substituted. By default, carbons , and , known as the meta positions are the only ones nucleophilic enough to carry out this reaction.

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