Chapter 11: Converting Alcohol Group to Alkyl Halide/Alkyl Tosylates

When the -OH functional group is involved, what is the FIRST thing that must happen?

The -OH functional group HAS to be converted into a BETTER leaving group

When the classification of carbon is involved, what is the PREFERRED order?

Tertiary over secondary, over primary

When SN2 reactions are involved to turn -OH functional groups to alkyl halides/tosylates, what is the DEGREE of carbon that is MOST preferred?

PRIMARY alcohols are loved

When SN1 reactions are involved to turn -OH functional groups to alkyl halides/tosylates, what is the DEGREE of carbon that is MOST preferred?

Secondary AND tertiary alcohols are loved

What ACIDS are MOST reactive when collaborating with -OH functional group?

HI>HBr>HCl

Out of the three acids listed, why is HCL the worst to react as a nucleophile?

When a PRIMARY alcohol is involved, chlorine can only react if there is an ADDITIONAL Lewis acid catalyst such as ZnCl2

When STEREOCHEMISTRY is involved, WHICH functional group is affected and what does this group react with?

The -OH group experiences manipulations in stereochemistry; the -OH is reacting with H-X

INVERSION of stereochemistry on the -OH functional group occurs in WHICH reaction and WHAT degree of carbon?

It occurs during the SN2 reaction with the PRIMARY alcohol

RACEMIZATION occurs in the -OH functional group in WHICH type of reaction mechanism and WHAT is the DEGREE of the carbon?

SN1 reaction with SECONDARY or TERTIARY CARBONS

During the SN1 mechanism, what is the CLASS of alcohols involved and CLASS of nucleophiles?

Secondary/tertiary alcohols are involved; MODERATE to WEAK nucleophiles are involved

What are the THREE steps for SN1 mechanism with H-X?

1) -OH group is protonated

2) Bond between C-O is broken

3)Bond between C-X forms

During SN1 mechanism with H-X, a carbocation forms. When does the carbocation form?

It is formed when the bond between the carbon and oxygen atom breaks. This is the SLOW step

During SN2 mechanism with H-X, what is the DEGREE of alcohol that is involved?

A PRIMARY alcohol

What are the TWO steps to occur during a SN2 mechanism?

1) protonation of the -OH functional group

2) C-O bond breaks while C-X bond forms