Exam 2 Flashcards
What are the characteristics of strongly activating substituents (Electron Donating Group) and directing energy?
–NH_2, –NR_2, –OH, –O^– ; o-, p- directing
Strongly activating groups are ortho- and para-directing.
List the moderately activating substituents (Electron Donating Group) and directing energy.
–NHCOR, –OR, –OCOR ; o-,p- directing
Moderately activating groups are also ortho- and para-directing.
What are weakly activating substituents (Electron Donating Group) and directing energy?
–R (alkyl), –Ph ; o-,p- directing
Weakly activating groups are ortho- and para-directing.
Identify a neutral substituent.
–H
Neutral substituents do not activate or deactivate the aromatic compound.
What are weakly deactivating substituents (Electron Withdrawing Group) and directing energy?
–Halide (F, Cl, Br, I) ; o-,p- directing
Weakly deactivating groups are ortho- and para-directing.
List the moderately deactivating substituents (Electron Withdrawing Group) and directing energy.
–COOR, –COR, –CHO, –COOH, –SO3H, –CN ; meta- directing
Moderately deactivating groups are meta-directing.
What are strongly deactivating substituents (Electron Withdrawing Group) and directing energy?
–CF_3, –CCl_3, –NO_2, –⊕^NR_3 ; meta-directing
Strongly deactivating groups are meta-directing.
True or False: Activators are meta-directing.
False
Activators are ortho- and para-directing.
True or False: Halogens are meta-directing deactivators.
False
Halogens are weakly deactivating and ortho- and para-directing.
Activators structures
Deactivators structures
Ortho attack
Meta attack
Para attack
No rxn for Electrophilic Aromatic Substitution
Electrophilic Aromatic Substitution
Halogenation - Electrophilic Aromatic Substitution
Nitration - Electrophilic Aromatic Substitution
Sulfonation - Electrophilic Aromatic Substitution
Fridel-Crafts Alkylation - Electrophilic Aromatic Substitution
With 1 degree R-X - Electrophilic Aromatic Substitution
Fridel-Crafts Acylation - Electrophilic Aromatic Substitution
Reduction - Electrophilic Aromatic Substitution
Reduction of Alkyl Group - Electrophilic Aromatic Substitution
Clemenson reduction: Zn/Hg / HCl
Wolf-Kisner: NH2NH2 / KOH
Group reactivity - Electrophilic Aromatic Substitution
Activator attack
Deactivator attack
Deactivator (halogen) attack
Weisenheimer Intermediate - Nucleophilic substitution
Benzyne intermediate - Neutrophillic substitution
Reduction of benzene - hydrogenation
Aldehydes and Ketones
Aldehyde Nomenclature
Ketone Nomenclature
Ozonolysis of alkene - Synthesis of Aldehydes
Oxidation of Secondary Alcohols - Synthesis of Ketones
Friedel-Crafts Acylation - Synthesis of Aldehydes
Rxn’s of Aldehydes and Ketones - Nucleophilic Addition Reactions
Nucleophiles in Nucleophilic Addition Reactions
Oxidation - Nucleophilic Addition Reactions
Formaldehyde to formalin
The conjugate acid to base ie H2O and OH-
Aldehyde to diol
Aldehyde rxn
Ketone rxn
Reduction - Aldehydes and Ketones
Carboxylic Acid Nomenclature and Properties
Nitrile Nomenclature and Properties
Synthesis of Carboxylic Acids: Ozonolysis of alkyne
Synthesis of Carboxylic Acids: Oxidation of alkene
Synthesis of Carboxylic Acids: Oxidation of Primary alcohol
Synthesis of Carboxylic Acids: Oxidation of aldehyde
Synthesis of Carboxylic Acids: Oxidation of alkyl benzene
Synthesis of Carboxylic Acids: Hydrolysis of Nitrile
Synthesis of Carboxylic Acids: Carboxylation of Grignard Reagent
Synthesis of Nitrile: SN2 of alkyl halide
Synthesis of Nitrile: Dehydration of Amides
Nucleophilic Aromatic Substitution and Elimination-Addition