Structural effects on reactivity

Nucleophile

the electron-rich, nucleus loving, and donates electrons

OH-, CL-

examples of nucleophilic

electrophilic

electron-poor, electron-loving, accept electrons

carbocations, carbonyl carbon, alkyl halides

example of electrophiles

Unimolecular nucleophilic substituion

SN1

In _________ or ____, it is fast because there is a presence of the tertiary alpha carbon

Bimolecular nucleophilic substitution

In _________ or ____, it is fast because there is a presence of the primary alpha carbon

chemical reactivity

it describes the behavior in which it decomposes of forms new substances whether it is substitution to form new products

Steric hindrance

slowing of chemical reactions due to steric bulk

Structural factors of carbocation stability

Inductive effects, hyperconjugation, and resonance

positively changed ion

electrophile

reactive

Carbocation is a ______________ which means it’s a ________, so it’s ___________

Electron donating group

stabilizes

______, which are the alkyl, donates electrons, and it (stabilizes or destabilizes _______ the carbocation

Electron withdrawing group

destabilizes

_________, which are the halogens, pull electrons, so it (stabilizes or destabilizes) carbocations

hyperconjugation

stable

More alkyl groups → more C-H bonds or electron donation, more _______ → more (stable or not stable)______ carbocation

Delocalized

Resonance

when the structure is spreads out the positive charge, so it became more balance and stable, it’s called ______, meaning it has _________

sp3 hybridized carbons

SN! and SN2 have both _____

Aromatic rings

_______ are highly stable and resistant to oxidation

Sn1

1. Tertiary

2. Carbocation is stable

3. weak nucleophile

4. Polar protic

Unimolecular nucleophilic substitution

Taking places in TWO steps:

1. breaking carbon and the LG bond

2. formation of intermediate carbocation with a FAST addition of a nucleophile

Bimolecular nucleophilic substitution

Single concerted step only. Attack of the nucleophile on the backside of the carbon-LG group bond and straight to the product

Nucleophilic substitution

reactions between carbon and a leaving group is broken, then a new bond between carbon and a nucleophile is formed

Sodium iodide in acetone

________ is a SN2 test because of its aprotic solvents and steric hindrance

Alcoholic silver nitrate test

________ is a SN1 test because of protic solvents anf carbn stability

Lucas test

Carbocation stability

_________ favors tertiary carbon because of ________

Alkaline potassium permanganate

It is a oxidizing agent for aromatic, however it doesnt react because of __________ and _____________

primary, benzylic, and alpha-halo acids

Sodium Iodide in acetone only works on ___________

aryl halides

electron poor carbons

Sodium Iodide in acetone fails on ___________

the carbocation is stabilized

Benzylic>Tertiary>Secondary

Alcoholic silver nitrate only works if ___________

no carbocation is possible

aryl halides and strong EDG

Alcoholic silver nitrate fails if ___________

Zinc chloride

In Lucas test, the ________ promotes leaving group departure

Zinc chloride and concentrated hydrochloric acid

Lucas reagent are _______ and ________

alkaline potassium permanganate

alkenes

benzylic side chains

The __________ oxidizes the __________ and activated the _______

white-yellow precipitate

Positive result in sodium iodide in acetone

turbidity, then white precipitate

Positive result in ethanolic silver nitrate test

Immediate cloudness

Positive result in lucas test

purple to brown solution

Positive result in Alkaline potassium permanganate