Term
| alcohols contain a ___ bonded to an ___ |
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Definition
| hydroxyl group (OH); sp3 hybridized Carbon atom |
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Term
| alcohols are classified as ____ based on the number of carbon atoms bonded to the carbon with the OH group |
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Definition
| primary, secondary, or tertiary |
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Term
| Compounds having a hydroxy group on an sp2 hybridized carbon are classified as ___ or ____ |
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Definition
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Term
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Definition
| an OH group on a carbon of a C-C double bond |
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Term
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Definition
| an OH group on a benzene ring |
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Term
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Definition
| two alkyl groups bonded to an oxygen atom |
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Term
| an ether is ___ if the two alkyl groups are the same, and ___ if they are different |
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Definition
| symmetrical; unsymmetrical |
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Term
| ___ are ethers having the oxygen atom in a three member ring. |
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Definition
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Term
| epoxides are also called ___ |
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Definition
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Term
| alcohols and ethers have a ___ shape |
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Definition
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Term
| the bond angle around the O atom in an alcohol or ether is ___ |
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Definition
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Term
| the COC bond angle of an epoxide must be ___ |
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Definition
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Term
| epoxides have ____, making them ____ |
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Definition
| angle strain; much more reactive than other ethers |
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Term
| alcohols are capable of ____ bonding |
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Definition
| intermolecular hydrogen bonding |
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Term
| Increasing the number of R groups around the Carbon atom bearing the OH group, ______ |
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Definition
| decreases the ability to hydrogen bond |
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Term
| for compounds of comparable molecular weight, the ___ the intermolecular forces, the ___ the bp or mp |
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Definition
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Term
| BP's ___ as the extent of hydrogen bonding ____ |
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Definition
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Term
| alcohols, ethers, and epoxides having less than or equal to 5 C's are _____ |
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Definition
| H2O soluble because they each have an oxygen atom capable of hydrogen bonding to the H2O |
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Term
| alcohols, ethers, and epoxides having greater than 5 C's are _____ |
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Definition
| H2O insoluble because the nonpolar alkyl portion is to large to dissolve in H2O |
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Term
| ranking of intermolecular foces |
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Definition
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Term
| alcohols, ethers, and epoxides of any size are ___ in organic solvents |
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Definition
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Term
| alcohols and ethers are both common products of ____. They are synthesized from alkyl halides by ___ reactions using strong nucleophiles |
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Definition
| nucleophilic substitution; Sn2 |
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Term
| because the mechanism is Sn2, the preferred path uses the _____ |
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Definition
| less sterically hindered halide |
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Term
| a ___ nucleophile is needed to synthesize an alcohol, and salts such as NaOH and KOH |
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Definition
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Term
| an ____ is needed to make an ether |
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Definition
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Term
| when an organic compound contains both a hydroxy group and a halogen atom on adjacent carbon atoms, an ______ |
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Definition
| intramolecular version of this reaction forms an epoxide |
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Term
| the starting material for the two step sequence of epoxide synthesis is a ____ |
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Definition
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Term
| -OH is a ___ base, and therefore a ___ leaving group |
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Definition
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Term
| for an alcohol to undergo a nucleophilic substitution or elimination reaction, the OH group must be ____; this can be done by reaction with ____ |
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Definition
| converted into a better leaving group; acid |
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Term
| the protonation of -OH makes ___, therefore a ___ leaving group |
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Definition
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Term
| ___ are formed by beta elimination |
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Definition
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Term
| ___ are formed by nucleophilic substitution |
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Definition
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Term
| ethers do not contain a ____ |
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Definition
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Term
| removing water from an alcohol is a ___ reaction |
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Definition
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Term
| dehydration is a ____ reaction, in which the elements of ___ and ___ are removed from the _____ |
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Definition
| Beta elimination; OH; H; alpha and beta carbon atoms |
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Term
| dehydration is typically carried out using ____ or ____ |
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Definition
| H2SO4 and other strong acids or POCl3 |
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Term
| ____ alcohols dehydrate more readily |
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Definition
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Term
| when an alcohol has two or three different beta carbons, dehydration follows the ____ |
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Definition
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Term
| 2 and 3 degree alcohols react by the ___ mechanism, whereas 1 degree alcohols react by the ___ mechanism |
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Definition
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Term
| The E1 dehydration of 2 and 3 degree alcohols consists of ___ steps |
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Definition
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Term
| the dehydration of 2 and 3 degree alcohols occurs via the ___ mechanism with an added first step |
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Definition
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Term
| the added first step ____ |
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Definition
| protonates the OH group to make a good leaving group |
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Term
| with 1 degree alcohols, dehydration follows the ___ mechanism |
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Definition
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Term
| a less stable carbocation can rearrange to a more stable carbocation by shift of a ___ or an ____ |
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Definition
| hydrogen atom; alkyl group |
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Term
| movement of a hydrogen atom is called a ____ |
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Definition
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Term
| movement of an alkyl group is called a ___ |
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Definition
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Term
| 1,2 shifts convert a ___ to a ___ |
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Definition
| less stable carbocation; more stable carbocation |
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Term
| the more stable carbocation is the more ____ |
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Definition
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Term
| rearrangements can occur whenever a ___ is formed as a _____; meaning any ___ or ___ reaction |
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Definition
| carbocation; reactive intermediate; SN1; E1 |
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Term
| the reaction of alcohols with ___ is a general method to prepare ____ |
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Definition
| HX; 1,2, and 3 degree alkyl halides |
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Term
| ___ alcohols usually react more rapidly with HX |
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Definition
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Term
| methyl and 1 degree ROH form RX by the ___ mechanism |
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Definition
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Term
| 2 degree and 3 degree ROH form RX by the ___ mechanism |
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Definition
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Term
| the reactivity of hydrogen halides increases with _____ |
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Definition
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Term
| Sn2 reaction have ___ at the stereogenic center |
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Definition
| inversion of stereochemistry |
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Term
| Sn1 reactions yield a _____ |
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Definition
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Term
| because carbocations are formed in the Sn1 reaction of 2 and 3 degree alcohols with Hx, ____ are possible |
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Definition
| carbocation rearrangements |
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Term
| one degree and two degree alcohols can be converted to alkyl halides using ____ and ____ |
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Definition
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Term
ROH->RCl with HCL reagent
- useful for ___
- ___ mechanism for 2 and 3 degree ROH; ___ mechanism for CH3OH and 1 degree ROH |
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Definition
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Term
ROH->RCl with SOCl2 reagent
-best for ____
- ___ mechanism |
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Definition
- ch3oh and 1 and 2 degree ROH
- sn2 mechanism |
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Term
ROH->RBr with HBr reagent
- useful for ___
- ___ mechanism for 2 and 3 degree ROH; ___ mechanism for CH3OH and 1 degree ROH |
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Definition
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Term
ROH->RBr with PBr3 reagent
-best for ____
- ___ mechanism |
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Definition
- ch3oh and 1 and 2 degree ROH
- sn2 mechanism |
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Term
ROH->RI with HI reagent
- useful for ___
- ___ mechanism for 2 and 3 degree ROH; ___ mechanism for CH3OH and 1 degree ROH |
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Definition
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Term
| alcohols can also be converted to ____ |
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Definition
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Term
| an alkyl tosylate is composed of two parts: |
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Definition
| the alkyl group R and the tosyl group (CH3C6H4SO2-) |
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Term
| because alkyl tosylates have good leaving groups, they undergo _____ |
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Definition
| both nucleophilic substitution and beta elimination |
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Term
| generally alkyl tosylates are treated with strong nucleophiles and bases, so that the method of sub is ___, and the mechanism of elimination is ___ |
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Definition
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Term
| summary of sub and e reactions with alcohols: the OH group is converted into a better leaving group by treatment with ____. The resulting product undergoes ___ depending on reaction conditions |
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Definition
| acid or another reagent; elimination or substitution |
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Term
| ethers can only react with ___ and ___ because they are strong acids with sources of good nucleophiles. |
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Definition
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Term
| when ethers react with HBr or HI, ___ are cleaved and ___ are formed as products. |
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Definition
| both C-O bonds; two alkyl halides |
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Term
| because both C-O bonds are broken, ___ reactions occur |
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Definition
| two successive nucleophilic substitution reactions occur. |
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Term
| the mechanism of either cleavage is ___ or ___ depending on the identity of R |
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Definition
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Term
| with a 2 or 3 degree alkyl group bonded to the ether oxygen, the C-O bond is cleaved by the ___ mechanism. with methyl or 1 degree R groups, the CO bond is cleaved by the ___ mechanism |
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Definition
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Term
| strong nucleophiles that open epoxides occur via the ___ mechanism |
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Definition
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Term
| the nucleophile opens the epoxide ring from the ____ |
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Definition
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Term
| in an unsymmetrical epoxide, the strong nucleophile attacks the epoxide at the ___ |
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Definition
| less substituted carbon atom |
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Term
| with an acid, the nucleophile attacks the epoxide at the ____ |
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Definition
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