Term
| The fact that the rate of the SN2 reaction diminishes drastically when the reacting center changes from primary to secondary to tertiary pertains only to _____ substitution |
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Definition
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Term
| Solvolysis is a transformation in which a substrate undergoes substitution by _____ molecules |
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Definition
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Term
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Definition
| when the solvent in solvolysis is water |
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Term
| For solvolysis reactions, the order of reactivity of a substrate is _____ from that found under SN2 reactions |
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Definition
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Term
| In solvolysis reactions, what is the order of reactivity of primary, secondary, and tertiary halides? |
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Definition
| tertiary > secondary > primary |
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Term
| Solvolysis reactions follow a _____ rate law |
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Definition
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Term
| Are solvolysis reactions stereospecific? |
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Definition
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Term
| The rate of the SN2 reaction is proportional to the concentration of _____ |
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Definition
| the substrate and the nucleophile |
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Term
| The rate of solvolysis is proportional to the concentration of _____ |
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Definition
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Term
| unimolecular nucleophilic substitution (AKA SN1) |
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Definition
| solvolysis; only 1 molecule participates in the rate-determining step |
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Term
| Does the rate of an SN1 reaction depend on the concentration of the nucleophile? |
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Definition
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Term
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Definition
| a hydrocarbon that contains a positively charged central carbon atom attached to three other groups and bearing only an electron sextet |
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Term
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Definition
| the conjugate acid of an alcohol; when the carbocation is bonded to by water |
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Term
| Why can tertiary halides not undergo SN2 reactions? |
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Definition
| they are to Sterically bulky |
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Term
| SN1 or SN2 mechanism?: tertiary halides |
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Definition
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Term
| SN1 or SN2 mechanism?: primary haloalkanes |
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Definition
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Term
| SN1 or SN2 mechanism?: secondary haloalkanes |
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Definition
| either route; depends on conditions |
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Term
| Carbocation stability is linked with _____ |
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Definition
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Term
| For secondary haloalkanes, if we use a substrate carrying a very good leaving group, a poor nucleophile, and a polar protic solvent, then _____ substitution is favored |
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Definition
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Term
| For a secondary haloalkane, if we employ a high concentration of a good nucleophile, a polar aprotic solvent, and a haloalkane bearing a reasonable leaving group, than _____ substitution predominates |
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Definition
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Term
| 2 conditions that must be satisfied before dissociation of a carbon-halogen bond into ions can occur |
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Definition
1. the carbon atom must be secondary or tertiary so that the carbocation has sufficient thermodynamic stability to form
2. the reaction must take place in a polar solvent capable or interacting with & stabilizing both positive & negative ions |
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Term
| What is meant by saying that the SN2 process is "stereospecific"? |
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Definition
| reaction of a single stereoisomeric substrate gives a single stereoisomeric product |
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Term
| In contrast with SN2 reactions, virtually all reactions that proceed via the SN1 mechanism at a stereocenter give _____ |
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Definition
| mixtures of stereoisomers |
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Term
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Definition
| starting from a haloalkane, the removal of HX with the simultaneous generation of a double bond |
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Term
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Definition
| unimolecular elimination reactions |
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Term
| E1 rate depends on the concentration of _____ |
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Definition
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Term
| The rate-determining step in the E1 process is the same as that in _____ reactions |
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Definition
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Term
| What is the rate-determining step in E1 reactions? |
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Definition
| dissociation to a carbocation |
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Term
| In E1 reactions, what is the second step of the mechanism (comes right after dissociation to a carbocation)? |
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Definition
| loss of a proton from a carbon adjacent to the one bearing the positive charge |
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Term
| Any hydrogen positioned on _____ can participate in the E1 reaction |
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Definition
| any carbon next to the center bearing the leaving group |
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Term
| Which is the major product and which is the minor product when E1 and SN1 reactions are both possible? |
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Definition
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Term
| SN1, SN2, E1, or E2: good but weakly basic nucleophiles |
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Definition
| SN2 with primary and secondary halides, SN1 with tertiary substrates |
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Term
| SN1, SN2, E1, or E2: weak nucleophiles |
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Definition
| SN1 but react with only secondary & tertiary halides (E1 is minor side reaction) |
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Term
| SN1, SN2, E1, or E2: branched primary substrates |
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Definition
| equal amounts of SN2 and E2 |
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Term
| SN1, SN2, E1, or E2: branched secondary substrates |
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Definition
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Term
| SN1, SN2, E1, or E2: tertiary halide, neutral/weakly basic conditions |
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Definition
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Term
| SN1, SN2, E1, or E2: tertiary halide, strong base |
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Definition
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Term
| SN1, SN2, E1, or E2: methyl, poor nucleophile |
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Definition
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Term
| SN1, SN2, E1, or E2: methyl, any decent nucleophile |
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Definition
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Term
| SN1, SN2, E1, or E2: primary substrate, poor nucleophile |
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Definition
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Term
| SN1, SN2, E1, or E2: primary substrate, good nucleophile |
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Definition
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Term
| SN1, SN2, E1, or E2: primary substrate, hindered nucleophile |
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Definition
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Term
| SN1, SN2, E1, or E2: branched primary substrate, poor nucleophile |
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Definition
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Term
| SN1, SN2, E1, or E2: branched primary substrate, weakly basic |
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Definition
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Term
| SN1, SN2, E1, or E2: branched primary substrate, strongly basic |
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Definition
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Term
| SN1, SN2, E1, or E2: secondary substrate, poor nucleophile |
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Definition
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Term
| SN1, SN2, E1, or E2: secondary substrate, weakly basic |
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Definition
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Term
| SN1, SN2, E1, or E2: secondary substrate, strongly basic |
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Definition
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Term
| SN1, SN2, E1, or E2: tertiary substrate, poor nucleophile |
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Definition
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Term
| SN1, SN2, E1, or E2: tertiary substrate, weakly basic |
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Definition
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Term
| SN1, SN2, E1, or E2: tertiary substrate, strongly basic |
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Definition
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