MCAT Organic Chemistry Review

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11 Terms

1

How do we name alcohols when they are the highest priority group? What if they aren’t?

If the alcohol is the highest priority group, the molecule drops the -e and gets an -ol suffix.

If it is not the highest priority group, then it is named as a substituent using the prefix hydroxy-.

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2

What do ortho, para, and meta mean?

Ortho means the functional groups are on adjacent carbons of a benzene ring. If the groups are separated by a single carbon, then they are meta. If they are on opposite sides of the benzene ring, they are para.

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3

How to turn a primary alcohol into an aldehyde?

Add pyridinium chlorochromate (PCC)

<p>Add pyridinium chlorochromate (PCC)</p>
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4

How to to turn a secondary alcohol into a ketone?

Add PCC or a strong oxidizing agent like chromium VI, or sodium or potassium dichromate salts (Na2Cr2O7, K2Cr2O7).

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5

How to turn a primary alcohol into a carboxylic acid?

Add a strong oxidizing agent like chromium VI, or sodium or potassium dichromate salts (Na2Cr2O7, K2Cr2O7).

<p>Add a strong oxidizing agent like chromium VI, or sodium or potassium dichromate salts (Na2Cr2O7, K2Cr2O7). </p>
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6

What is the Jones Oxidation?

Chromium trioxide (CrO3) is dissolved with dilute sulfuric acid and acetone. This is a very strong oxidizing agent and it turns primary alcohols into carboxylic acids and secondary alcohols into ketones.

<p>Chromium trioxide (CrO3) is dissolved with dilute sulfuric acid and acetone. This is a very strong oxidizing agent and it turns primary alcohols into carboxylic acids and secondary alcohols into ketones. </p>
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7

Mesylate

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8

Tosylate

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9

Acetal and Ketal

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10

What happens when a phenol is treated with an oxidizing agent?

You make a quinone.

<p>You make a quinone. </p>
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11

Adding methylsulfonyl chloride or toluene sulfonic acid to an alcohol will…

Create a protecting group (either a mesylate or tosylate) that prevents the alcohol from reacting. This can be removed with a strong acid.

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