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Organic Chemistry by Brown, Iverson, Anslyn, Foote | Mayya's Study Guide | Chapter 10

Chapter 10: Alcohols


Table of contents of main topics:



Nomenclature of Alcohols

  1. Find the longest continuous carbon chain and start numbering from the end closest to the OH group. End the parent chain name with "ol" and put a number in front of the name signifying the carbon to which OH is attached.

  2. If the OH group is on a ring, start counting from the carbon that has the OH group.

  3. Proceed with naming substituted just like we did for alkanes and put the name together with substituents first (in alphabetical order) followed by the name of the parent.

  4. If there are multiple OH groups, use "diol" (2), and "triol"(3)...

  5. For molecules containing a double bond and an alcohol use parent name ending in "en"-#-"ol"


Alcohols can be classified as:

Primary = OH is on a carbon that is attached to one carbon only

Secondary = OH is on a carbon that is attached to two other carbons

Tertiary = OH is on a carbon attached to three more carbons


Reaction of Alcohols with Active Metals


Alcohols will get deprotonated when reacting with metals such as NaH.

Reaction of Alcohols with Active Metals
Reaction of Alcohols with Active Metals


Conversion of Alcohols to Haloalkanes and Sulfonates (How to make alcohol into a good leaving group).

Alcohols are very poor leaving groups. We oftentimes need to convert an alcohol into a good leaving group to do further reactions on the molecule. The reagents that make alcohol into a good leaving group are: HCl, HBr, HI, TsCl, PBr3 and SOCl2.


The reaction of alcohol with HBr or HCl yields Br or Cl instead of the OH group. Please note that these reactions are capable of rearrangements and do not always give the desired product.

Tertiary and secondary alcohols will reach with HX with Sn1, while primary alcohols with no extensive beta branching will undergo SN2.


Mechanism of the reaction of alcohol with HCl
Mechanism of the reaction of alcohol with HCl


The reaction of alcohol with TsCl (tosyl chloride) produces ROTs ( alkyl tosylate). OTs is an excellent leaving group. In this reaction, the stereochemistry of OH as it gets converted to OTS remains the same. For example, if OH was on a wedge, OTs would be on a wedge as well.


Preparation Of Sulfonate Esters Using sulfonyl chloride  (OH into OTs)
Preparation Of Sulfonate Esters Using sulfonyl chloride (OH into OTs)

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