Exam 1 Organic Chemistry 2

Aldehydes + Grignard

secondary OH

Ketones + Grignard

Tertiary OH

Formaldehyde + Grignard

Primary Alcohol

Ester/Acid Chlorides + Grignard

Tertiary OH

Nitriles (CN) + Grignard

Makes ketones

H2O will make

Just hydrogen

Whenever you the word “EXCESS” on the reagent

It’s mean use the reagent 2 TIMES

Carboxylic Acid /Aldehyde/Ketone/Ester + LiAlH4

Alcohols

OH-Ch2-Ch2-OH

Diol

What is a Diol

Protecting Group

What can transform Diol to carbonyl by ?

H+

Diol + H+

Carbonyl

Aldehyde + NaBH4, MeOH

Primary Alcohol

Aldehyde + H2/ Pt, Pd, Ni

Primary Alcohol

Aldehyde + LiAlH4/H2O

Primary Alcohol

Ketone + NaBH4, MeOH

Secondary Alcohol

Ketone + H2/ Pt,Pd,Ni

Secondary Alcohol

Ketone + LiAlH4/H2O

Secondary Alcohol

Carboxylic Acid + Excess LiAlH4/ H2O

Primary Alcohol

R-C=O-OMe + Excess LiAlH4/H2O

Primary Alcohol + MeOH

Secondary Alcohol + Na2Cr2O7/H2SO4, H2O

Ketone

R-OH + TMSCl/ Et3N

R-O-TMS

R-O-TMS + TBAF

R-OH

How do you make Carboxylic Acid from primary alcohol

Na2Cr2O7/H2SO4,H2O

How do you make Aldehyde from a Primary Alcohol

PCC/Ch2Cl2

How do you make Benzoquinone from phenol

Na2Cr2O7/H2SO4,H2O

Alkyl halide + NaOH

Primary OH

Primary Alcohol + TsCl, py

Primary OTS

Primary OTS + NaOH

Primary OH

Alkyl Tosylate abbreviated

OTS

Tertiary Alcohol

Tertiary Alcohol + Conc. H2SO4

OH will removed and form on Double Bond where the OH was

Tertiary Halogen + NaOH

Form double bond where the halogen was

Any tertiary halogen (alkyl halide) will form

Stable or unstable double bond

Tertiary OH + NaOH

Alkene where OH was removed

t-BuOK will form ?

Unstable Double Bond