Exam 2 Flashcards by Nydia Dixon

Q

What are the characteristics of strongly activating substituents (Electron Donating Group) and directing energy?

A

–NH_2, –NR_2, –OH, –O^– ; o-, p- directing

Strongly activating groups are ortho- and para-directing.

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Q

List the moderately activating substituents (Electron Donating Group) and directing energy.

A

–NHCOR, –OR, –OCOR ; o-,p- directing

Moderately activating groups are also ortho- and para-directing.

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Q

What are weakly activating substituents (Electron Donating Group) and directing energy?

A

–R (alkyl), –Ph ; o-,p- directing

Weakly activating groups are ortho- and para-directing.

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Q

Identify a neutral substituent.

A

–H

Neutral substituents do not activate or deactivate the aromatic compound.

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Q

What are weakly deactivating substituents (Electron Withdrawing Group) and directing energy?

A

–Halide (F, Cl, Br, I) ; o-,p- directing

Weakly deactivating groups are ortho- and para-directing.

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Q

List the moderately deactivating substituents (Electron Withdrawing Group) and directing energy.

A

–COOR, –COR, –CHO, –COOH, –SO3H, –CN ; meta- directing

Moderately deactivating groups are meta-directing.

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Q

What are strongly deactivating substituents (Electron Withdrawing Group) and directing energy?

A

–CF_3, –CCl_3, –NO_2, –⊕^NR_3 ; meta-directing

Strongly deactivating groups are meta-directing.

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Q

True or False: Activators are meta-directing.

A

False

Activators are ortho- and para-directing.

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Q

True or False: Halogens are meta-directing deactivators.

A

False

Halogens are weakly deactivating and ortho- and para-directing.

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Q

Activators structures

A

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Q

Deactivators structures

A

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Q

Ortho attack

A

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Q

Meta attack

A

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Q

Para attack

A

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Q

No rxn for Electrophilic Aromatic Substitution

A

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Q

Electrophilic Aromatic Substitution

A

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Q

Halogenation - Electrophilic Aromatic Substitution

A

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Q

Nitration - Electrophilic Aromatic Substitution

A

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Q

Sulfonation - Electrophilic Aromatic Substitution

A

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Q

Fridel-Crafts Alkylation - Electrophilic Aromatic Substitution

A

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Q

With 1 degree R-X - Electrophilic Aromatic Substitution

A

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Q

Fridel-Crafts Acylation - Electrophilic Aromatic Substitution

A

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Q

Reduction - Electrophilic Aromatic Substitution

A

Q

Reduction of Alkyl Group - Electrophilic Aromatic Substitution

A

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