Examen 1 Flashcards by Alondra Toro

contains a hydroxy group (OH) bonded to an sp3 hybridized carbon

alcohols

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hydroxy group on a sp2 hybridized carbon

enols and phenols

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two alkyl groups bonded to an oxygen atom

ethers

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ethers having the oxygen atom in a three membered ring
also called oxiranes
have angle strain, making them more reactive than ethers

epoxides

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have a bent shape like in H2O

alcohols and ethers

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both polar with a 109.5 angle

C-O and O-H bonds

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alcohols, ethers, and epoxides exhibit

dipole-dipole interactions

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alcohols are more polar than ethers and epoxides

intermolecular hydrogen bonding

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affect hydrogen bonding

steric factors

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the _____ the intermolecular forces, the ______ the boiling point or melting point

stronger; higher

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boiling ponts _______ as the extent of hydrogen bonding _______

increase

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alcohols, ethers, and epoxides having less than 5 carbons are

soluble

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CH3OH
extremely toxic

methanol

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(CH3)2CHOH
major component of rubbing alcohol

2- propanol

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HOCH2CH2OH
major component of antifreeze

ethylene glycol

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yield ethanol and form usable fuels

hydrolysis of starch and fermentation

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a crown ether- cation complex is called
the crown ether is the HOST and the cation is the GUEST

host-guest complex

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the ability of a host molecule to bind specific guest is called

molecular recognition

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the ability of crown ethers to complex cations can be exploited in
- the relatively unsolvated anion is extremely nucleophilic

nucleophilic substitution reactions

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alcohols and ethers are both common products of

nucleophilic substitution

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un alcoxido reacciona con un haluro de alquilo
less hindered path is preferred

Williamson ether synthesis

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para desabotonar un alcohol se necesita una

base fuerte

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is needed to make an ether

alkoxide salt

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organic compounds that contain both a hydroxy group and a halogen atom on adjacent carbons

halohydrins

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in halohydrins, an _____ version of the Williamson ether synthesis can occur to form epoxides

intramolecular

OH is a ___ leaving group

very poor

base débil o estable

buen grupo saliente

protonates the bad leaving groups and makes them good leaving groups

strong acid

a beta elimination reaction in which the elements of OH and H are removed from the alpha and beta carbons respectively - typically carried out using H2SO4 and other strong acids

dehydration

more substituted alcohols dehydrate more

easily

en una reacción de eliminación, se favorece la formación del alqueno mas sustituido

regla de zaitsev

the more substituted alkene is the ______ product when a mixture of constitutional isomers is possible

major

react by an E1 mechanism

2 and 3 alcohols

react by an E2 mechanism

1 alcohols

E1 mechanism

1. the O atom is protonated: protonation converts a poor leaving group into a good one 2. the C-O bond is broken: heterolysis of the C-O bond forms a carbocation 3. a C-H bond is cleaved and the pi bond is formed: a base removes a proton from a carbon adjacent to the carbocation

E2 mechanism

1. The O atom is protonated 2. The C-H and C-O bonds are broken and the pi bond is formed

favors product formation in dehydration

entropy

favors reactants

enthalpy

equilibrium will react to counteract any disturbance to the equilibrium

Le chatelier's principle

removing a product as it is formed drives the equilibrium to the _____ forming more product

right

a less stable carbocation will be converted into a more stable one

rearrangement

movement of a hydrogen atom

1,2-hydride shift

movement of an alkyl group

1,2- alkyl shift

carbocation rearrangement during dehydration

1 and 2: protonation of the oxygen atom 3: rearrangement of the carbocation by a 1,2- CH3 shift 4: loss of a proton to form the pi bond

can convert a less stable carbocation into a more stable carbocation

1,2 shift

- not unique to dehydration reactions - can occur whenever a carbocation is formed as a reactive intermediate

rearrangements

si el carbo cation esta en su estado de energía mas bajo (3) no hay que hacer más

rearreglos

do not occur with alcohols unless ^-OH is converted into a good leaving group

substitution reactions

mecanismo SN2

1. the O atom is protonated 2. the C-O bond is broken as the C-Br bond is formed

Sn1 mechanism

1. the O atom is protonated 2 and 3. the C-O bond is broken as the C-Br bond is formed (with a carbocation as the intermediate)

can be converted to alkyl halides using SOCL2 and PBr3

primary and 2 alcohols

converts alcohols into alkyl chlorides

SOCl2 thionyl chloride

converts alcohols into alkyl bromides

PBr3 phosphorus tribromide

are strong acids that are also good nucleophiles - form two alkyl halides

HBr y HI

when 2 or 3 alkyl groups are bonded to the ether oxygen, the C-O bond is cleaved by an

SN1 mechanism involving a carbocation

With methyl or 1 R groups, the C-O bond is cleaved by an

SN2 mechanism

do not contain a good leaving group contain a three- membered ring with 2 polar bonds

epoxides

achiral (optically inactive) reactants yield

achiral (optically inactive) products

- olefins - contain a double bond y su formula general es CnH2n

alkenes

have the double bond at the end

terminal alkenes

have at least one carbon atom bonded to each end of the double bond

internal alkenes

contain a double bond in a ring

cycloalkenes

- contain a triple bond - CnH2n-2

alkyne

triple bond introduces

two degrees of unsaturation

terminal alkynes

RC---CH

internal alkynes

RC---CR

- double bond consists of a pi bond and a sigma bond - each carbon is sp2 hybridized sand trigonal planar, with bond angles of approximately 120

alkene hybridization

- triple bonds consists of 2 pi bonds and 1 sigma bond - each carbon is sp hybridized with a linear geometry and bond angles of 180

alkyne bonding

pi bond is much ____ than the sigma bond of a C-C double bond

weaker

alkenes undergo

many reactions that alkanes do not

cycloalkanes having fewer than eight carbon atoms have a ___ geometry

cis

trans alkenes are generally more stable than ____ alkenes

cis

the rotation around the C-C double bond is

restricted

the stability of an alkene increases as the number of R groups

increases

has the general structural formula

CnH2n acyclic alkene

unsaturated hydrocarbons

alkenes

have the general formula

CnH2n cycloalkanes

Physical Properties of Alkenes

- Exhibit only weak van der Waals interactions - low melting points and boiling points. - Melting and boiling points increase as the number of carbons increases because of increased surface area - soluble in organic solvents and insoluble in water

Physical Properties of Alkynes

- same as alkenes

Cis/ trans Differ in Physical Properties

- cis-2-Butene has a higher boiling point (4 °C) than trans-2-butene (1 °C).

Examen 1 Flashcards

(80 cards)