Substituiton And Elimination Rxns Flashcards by Amaria Armour

Q

Strong Base + Weak Nucleophile + 1°

A

E2

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Q

Strong Base + Weak Nucleophile + 2 °

A

E2

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Q

Strong Base + Weak Nucleophile + 3 °

A

E2

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Q

Strong Base + Strong Nucleophile + 1 °

A

E2 = Minor Product
SN2 = Major Product

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Q

Strong Base + Strong Nucleophile + 2 °

A

E2 = Major product
SN2 = Minor Product

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Q

Strong Base + Strong Nucleophile + 3 °

A

E2

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Q

Weak Base + Strong Nucleophile + 1 °

A

SN2

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Q

Weak Base + Strong Nucleophile + 2°

A

SN2

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Q

Weak Base + Strong Nucleophile + 3 °

A

SN1

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Q

Weak Base + Weak Nucleophile + 1 ° or 2 °

A

Typically too unstable to form

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Q

Weak Base + Weak Nucleophile + 3 °

A

SN1 and E1 (equally)

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Q

3 ° + weak Nucleophile/ weak base

A

SN1/E1

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Q

2 ° + weak Nucleophile/weak base

A

SN1/E1, just not efficient or very stable

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Q

3 ° + strong Nucleophile/ weak base

A

SN1

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Q

2 ° + strong Nucleophile/ weak base

A

SN2

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Q

1 ° + strong Nucleophile/ weak base

Study These Flashcards

A

SN2

Q

CH3 (methyl) + strong Nucleophile

Study These Flashcards

A

SN2

Q

3 ° + strong base

Study These Flashcards

A

E2

Q

Reminder: Does SN2 occur at 3 °?

Study These Flashcards

A

No, 3 ° for SN2 is unstable
(CH3 > 1 ° > 2 °)

Q

2 ° + strong Nucleophile/ strong base

Study These Flashcards

A

E2 = major
SN2 = minor

Q

1 ° + strong Nucleophile/ strong base

Study These Flashcards

A

SN2 = major
E2= minor

Q

2 ° + strong, bulky base

Study These Flashcards

A

E2

Q

1 ° + strong, bulky base

Study These Flashcards

A

E2

Q

Reminder: what rxns do not occur at 1°?

Study These Flashcards

A

SN1 and E1

Weak Nucleophiles, Weak Bases

H20 (water) ROH (alcohol) RCOOH (carboxylic acid)

Strong Nucleophiles, Weak Bases

CN-, N3-, Cl-, Br-, I-, RS-, HS- (hydro sulfide), RSH (thiol), H2S, RNH2 (amine), R3P

Strong Nucleophile, Strong Base

OH-, RO- (alkoxide)

Strong, bulky base

t-buO- (tert butoxide), Et3N (trierhylamine), DBN, DBU…

SN2 Substrate Stability…

CH3 > 1 ° > 2 °

E2 Substrate Stability…

3 ° > 2 ° > 1 °

SN1 substrate stability

3 ° > 2 °

E1 substrate stability

3 ° > 2 °