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18 Cards in this Set
- Front
- Back
What's the structure of a methyl Alkyl Halide? |
SP3 hybridized Carbon bonded to 3 Hydrogens and one Halogen (X) |
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What's the structure of a primary Alkyl Halide? |
SP3 hybridized Carbon bonded to 1 R group, 2 Hydrogen, 1 Halogen (X) |
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What's the structure of a secondary Alkyl Halide? |
SP3 hybridized Carbon, 2 R groups, 1 Hydrogen, 1 Halogen (X) |
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What's the structure of a tertiary Alkyl Halide? |
SP3 hybridized Carbon, 1 Halogen (X), 3 R groups |
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What is the structure of an Allylic Halide? |
CH2CH2C-X (Chain of 3 Carbon, double bond between first two) |
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What is the general equation of a nucleophilic substitution reaction? |
R--X + Nu- ----> R--Nu + X- |
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Define the leaving group in a nucleophilic substitution reaction |
Typically Halogen, that breaks a bond with the carbon and keeps the electrons, typically forming a negatively charged species. |
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Characteristics of a Good Leaving group |
Halogen, weak base with strong conj. acid, more stable with the negative charge (so neutral when attached to C) |
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Periodic trend of leaving group ability |
Ability increases across a row and down a column |
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Rank the compounds in order of worse to better leaving group ability: HO-, H2N-, F-, H3C- |
H3C-<H2N-<OH-<F- |
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Characteristics of a good nucleophile |
Strong base, wants to attack an electrophile to share electrons/donate e- pair *affected by steric effects and solvent effects |
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General periodic trend of nucleophilicity |
decreases across a row and up a column (opposite trend of Leaving Group ability) |
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Is water a better nucleophile or leaving group? Why? |
Leaving group, when attached to a carbon, it has a positive charge, wants electrons. |
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What is steric hinderance in nucleophilicity? |
When there are bulkier groups on the nucleophile, it is worse at bonding to the C--X group. |
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Example of a sterically hindered Nucleophile |
t-buOK (tert-butoxide) has too make CH3 groups on it to be able to attack the structure |
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What are solvent effects? |
Depending on if the solvent is protic or aprotic, nucleophile trends are affected |
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Protic solvent, examples, effects on periodic trend of nucleophile |
Can form Hydrogen bonds (contains O-H or N-H bonds), examples are: Water, MeOH, EtOH, CH3COOH, tBuOH. Nucleophilicity increases with size of the ion. |
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Example of aprotic solvents |
Acetone, THF, DMF, DMSO |