Term
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Definition
| an organic compound that contains a hydroxy (-OH) group |
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Term
| bond angles of water and alcohol about the O atom |
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Definition
| 104.5° for water and 108.9° for alcohol |
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Term
| O-H bond length vs. C-O bond length |
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Definition
| C-O bond length longer because C is bigger than H |
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Definition
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Definition
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Definition
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Definition
contains a hydroxy group bonded directly to an aromatic (benzene) ring
[image] |
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Term
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Definition
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Term
| rules for naming alcohols |
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Definition
1: name the longest carbon chain that the -OH group is located on; this is the parent chain
2: replace the last -e with the suffix -ol
3: number the parent chain starting nearest to the -OH group
4: use a number to indicate position of the -OH group
5: hydroxy (-OH) group takes precedent over double and triple bonds
6: name the substituents just like you would for an alkane |
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Term
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Definition
| -OH (when there's a functional group of higher priority) |
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Term
| table of functional group priorities |
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Definition
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Term
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Definition
| usually a 1,2-diol, or vicinial diol |
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Term
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Definition
| has its 2 hydroxy groups on adjacent C atoms |
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Term
| how glycols aka vicinial diols are usually synthesized |
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Definition
| by hydroxylation of alkenes, using peroxyacids, osmium tetroxide, or potassium permanganate |
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Term
| physical state of alcohols |
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Definition
usually liquid, up to about 11 or 12 C atoms
some highly branched isomers are solids at room temperature |
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Term
| boiling points of alcohols, ethers, and alkanes |
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Definition
| alcohols > ethers > alkanes |
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Term
| the intermolecular forces that occur between alcohol molecules |
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Definition
-H bonding
-dipole-dipole attractions |
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Term
| why ethers, such as dimethyl ether, can't do H bonding |
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Definition
because they have no O-H hydrogens
[image] |
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Term
| why tert-butyl alcohol is unusually soluble for a 4-C alcohol |
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Definition
| because of its compact, spherical shape |
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Term
| why phenol is unusually soluble for a 6-C alcohol |
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Definition
| because of its compact shape and particularly strong H bonding |
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Term
| minimum-boiling azeotrope |
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Definition
| mix of liquids that boils at a lower temperature than either of its components |
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Term
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Definition
| the anion that results when an alcohol is deprotonated |
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Term
| how alkoxide ions are formed |
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Definition
a strong base deprotonates the hydroxy (-OH) group
[image] |
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Term
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Definition
| acid-dissociation constant |
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Term
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Definition
| Ka = ([H3O+][RO-]) / [ROH] |
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Term
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Definition
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Term
| the equilibrium that defines the acid dissociation constant (Ka) of an alcohol |
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Definition
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Term
| the Ka's for most alcohols |
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Definition
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Term
| substitution vs. acidity of alcohol |
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Definition
| inversely related (more substituted means less acidic) |
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Term
| why more substituted alcohols are less acidic |
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Definition
| because greater substitution inhibits solvation of the alkoxide ion |
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Term
| alkoxides are ______ nucleophiles |
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Definition
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Term
| alkoxides are ______ bases |
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Definition
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Term
| how a Na alkoxide is formed |
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Definition
| R-O-H + Na --> R-O-Na= + 1/2H2 |
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Term
| substitution of an alcohol vs. rate of rxn with Na |
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Definition
| inversely related (more substituted alcohols react more slowly with Na) |
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Term
| why K is often used with secondary and tertiary alcohols |
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Definition
| because it's more reactive than Na, making the rxn faster |
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Term
| reagent that's often used when alcohols react slowly with both Na and K |
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Definition
| sodium hydride (NaH), often in THF solution |
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Term
| why phenol is more acidic than cyclohexanol |
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Definition
| because the phenoxide ion (deprotonated form) is more stable due to resonance |
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Term
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Definition
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Term
| how the phenoxide ion is formed |
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Definition
by putting it in an aqueous solution of NaOH or KOH
[image] |
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Term
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Definition
| organic compound that contains a covalent bond between a metal atom and a C atom |
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Term
| are terminal alkynes acidic or basic? |
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Definition
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Term
| how sodium acetylides are formed |
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Definition
| [image]
however, most alkyl and alkenyl groups aren't acidic enough to be deprotonated by sodium amide (NaNH2) |
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Term
| how substituted alkynes are formed |
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Definition
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Term
| how acetylinic alcohol is formed |
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Definition
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Term
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Definition
| organimetallic halides that have the empirical formula R-Mg-X |
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Term
| the types of alkyl halides that Grignard reagents can be made from |
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Definition
-primary alkyl halides
-secondary alkyl halides
-tertiary alkyl halides
-vinyl halides
-aryl halides
-allyl halides |
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Term
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Definition
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Term
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Definition
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Term
| alkyl halides (Grignard reagents) in order of reactivity |
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Definition
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Term
| how Grignard reagents are formed from alkyl halides |
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Definition
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Term
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Definition
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Term
| how Grignard reagents are made from allyl halides |
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Definition
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Term
| how organilithium reagents are made from alkyl halides |
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Definition
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Term
| how organilithium reagents are made from vinyl halides |
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Definition
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Term
| how organilithium reagents are made from aryl halides |
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Definition
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Term
| the type of solvent that must be used for ALL Grignard reactions |
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Definition
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Term
| Grignard and organolithium reagents are ______ bases |
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Definition
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Term
| Grignard and organolithium reagents are ______ nucleophiles |
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Definition
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Term
| the most useful nucleophilic additions that use Grignard and organolithium reagents |
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Definition
| addition to carbonyl (C=O) groups |
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Definition
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Definition
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Term
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Definition
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Term
| Grignard reaction mechanism |
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Definition
formation: [image]
reaction 1: [image]
reaction 2: [image] |
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Term
| some derivatives of carboxylic acids |
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Definition
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Term
| acid chlorides and esters are derivatives of... |
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Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Term
| what should the Grignard reagent attack to form a tertiary alcohol? |
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Definition
an acid chloride or ester
[image] or [image] |
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Term
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Definition
| ethyl formate (a type of formate ester) |
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Term
| what should the Grignard reagent attack to make a secondary alcohol with identical alkyl groups? |
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Definition
| a formate ester, such as ethyl formate |
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Term
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Definition
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Term
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Definition
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Term
| lithium dialkylcuprate aka Gilman reagent |
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Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
vinyl halides
a vinyl halide is when a halogen is bonded to a C with a double bond |
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Term
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Definition
[image]
a vinyl halide is when a halogen is bonded to a C with a double bond |
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Term
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Definition
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Term
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Definition
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Term
| Grignard reagents are ______ nucleophiles |
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Definition
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Term
| Grignard reagents are ______ bases |
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Definition
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Term
| organolithium reagents are ______ nucleophiles |
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Definition
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Term
| organolithium reagents are ______ bases |
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Definition
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Term
| how Grignard reagents react with water |
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Definition
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Term
| the type of acid-base rxns that are irreversible |
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Definition
| those where the pKa of the acids differ by about 10 or more |
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Term
| groups that protonate the Grignard or organolithium reagent |
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Definition
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Term
| groups that can be attacked by the Grignard or organolithium reagent |
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Definition
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Term
| what a hydride reagenty does |
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Definition
| adds a hydride ion (H:-) to reduce the carbonyl (ketone) group to an alkoxide ion without adding carbons |
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Term
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Definition
| lithium aluminum hydride (LAH) |
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Term
| lithium aluminum hydride (LAH) |
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Definition
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Term
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Definition
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Term
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Definition
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Term
| NaBH4 and LiAlH4 are ______ nucleophiles |
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Definition
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Term
| NaBH4 and LiAlH4 are ______ bases |
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Definition
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Term
| mechanism of hydride reduction of a carbonyl group using LAH |
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Definition
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Term
| can lithium aluminum hydride (LAH) be used in hydroxylic solvents (solvents containing an -OH group)? |
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Definition
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Term
| can sodium borohydride (NaBH4) be used in hydroxylic solvents (solvents containing an -OH group)? |
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Definition
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Term
| a good solvent to use for reduction rxns involving LAH |
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Definition
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Term
| why LAH is a much stronger reducing agent than sodium borohydride is |
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Definition
| because aluminum is less electronegative than boron |
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Term
| comparison of electronegativity differences in LAH and NaBH4 |
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Definition
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Term
| why NaBH4 is a more selective reducing agent than LAH is |
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Definition
| because it does not react with carbonyl groups that are less reactive than ketones or aldehydes |
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Term
| some more reactive carbonyl groups that NaBH4 will reduce |
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Definition
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Term
| some less reactive carbonyl groups that NaBH4 will not reduce |
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Definition
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Term
| some carbonyl groups that lithium aluminum hydride (LAH) will reduce |
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Definition
mostly all carbonyl groups discussed so far
-ketones
-aldehydes
-carboxylic acids
-esters |
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
| the product that forms if treated with NaBH4
[image] |
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Definition
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Term
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Definition
finely divided hydrogen-bearing form of nickel that can be used as a catalyst in catalytic hydrogenation of ketones and aldehydes
it is made by treating a nickel-aluminum alloy with a strong NaOH solution |
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Term
| how Raney Nickel is used in catalytic hydrogenation |
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Definition
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Term
| effect of Raney nickel vs. effect of NaBH4 |
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Definition
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