Test 3 Flashcards by Allie Skinkle | Brainscape

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syn addition

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trans glycol

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Syn addition

cis glycol

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syn addition

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syn addition

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anti-markovnikov

Br on less subs c

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markovnikov= OH on most subs C

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markovnikov= OH on most subs C

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anti-addition

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anti-addition

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syn addition, anti-markovnikov=OH on less subs C

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anti-addition

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anti-addition

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Other alkylating agents can be used: MeO and MeS

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K₂Cr₂O₇ in aqueous H₂SO₄ may also be used

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2^o alchohol most likely via SN1 so stereochem lost

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best with 1^o alcohols

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Best with 1^o alcohols

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poor nucleophiles/weak bases

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O with no formal charge

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Good nucleophiles/weak bases

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Cl^-, Br^-, I^-, NC^-, N₃^-, S^-, Se^- or CH₃COO^-, or N, S, Se with no formal charge

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Good Nucleophile/strong base

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1^o Carbon, poor Nuc/weak base

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no reaction

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2^o Carbon, poor Nuc/weak base

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95% Sn1

5% E1

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3^o Carbon, poor Nuc/weak base

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95% Sn1

5% E1

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1^o or 2^o Carbon, good Nuc/weak base

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Sn2

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3^o Carbon, good Nuc/weak base

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95% Sn1

5% E1

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1^o Carbon, good Nuc/strong base

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E2 w/ tert-butyl-oxide (bulky base), otherwise Sn2

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2^o or 3^o Carbon, good Nuc/strong base

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E2

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Sn2

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One Step: Nucleophile joins alpha carbon and leaving group leaves alpha carbon, inversion of stereochem

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Sn1

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Step 1: leaving group leaves alpha carbon

Step 2: Nucleophile joins alpha carbon

racemization

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E2

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One step: Base takes Beta hydrogen, pi bond forms between alpha and beta carbons, leaving group leaves alpha carbon

-H and LG have to be antiperiplanar

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E1

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Step 1: Leaving group leaves alpha carbon

Step 2: Base takes Beta hydrogen, pi bond forms between alpha and beta carbons

both cis and trans are made

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Good leaving groups

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Cl, Br, I, N⁺, O⁺, P⁺, S⁺, sulfonate