Chapter 6: Organic Halogen Compounds; …employees.oneonta.edu/odagomo/Chapter_6.pdfChapter 6:...
Transcript of Chapter 6: Organic Halogen Compounds; …employees.oneonta.edu/odagomo/Chapter_6.pdfChapter 6:...
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Chapter 6: Organic Halogen Compounds; Substitution and Elimination Reactions
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Nucleophilic Substitution
Examples of nucleophilic substitution reactions Nucleophile Substrate Leaving group
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Reaction of sodium ethoxide with bromoethane
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Nucleophilic Substitution Mechanism
SN2 Mechanism
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SN2 displacement reactions occurs with inversion of configuration. For example, if we treat (R)-2-bromobutane with sodium hydroxide, we obtain (S)-2-butanol
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Example; Predict the product of the SN2 reaction of cis-4-methylcyclohexyl bromide with cyanide ion
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Arrange the following compounds in order of decreasing SN2 reactivity toward sodium ethoxide
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The SN1 Mechanism
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Which of the following bromides will react faster with methanol (via SN1 reaction)? and what are the reaction products in each case.
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1. Negative ions are more nucleophilic, or better suppliers, than the corresponding neutral molecules.
HO- > HOH RS- >RSH RO- > ROH
2. Elements low in the periodic table tend to be more nucleophilic than elements above them in the same column
HS- > HO- I- > Br- > Cl- > F-
3. Across a row in the periodic table, more electronegative elements (the more tightly an element holds electron to itself) tend to be less nucleophilic.
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Which mechanism, SN1 or SN2, would you predict for each of the following reactions?
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Dehydrohalogenation, and Elimination Reaction; The E2 and E1 Mechanisms
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E1 mechanism
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Substitution and Elimination in Competition
Tertiary Halides
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Primary Halides
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t-butoxide
Ethoxide
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Secondary Halides
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Polyhalogenated Aliphatic Compounds
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Chlorofluorocarbons (CFCs aka Freons)
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Halons
CBrClF2 Bromochlorodifluoromethane (Halon-1211)
CBrF3 Bromotrifluoromethane Halon-1301