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Química orgánica 2 > Examen 1 > Flashcards

Examen 1 Flashcards

1
Q

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

A

alcohols

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2
Q

hydroxy group on a sp2 hybridized carbon

A

enols and phenols

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3
Q

two alkyl groups bonded to an oxygen atom

A

ethers

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4
Q
  • ethers having the oxygen atom in a three membered ring
  • also called oxiranes
  • have angle strain, making them more reactive than ethers
A

epoxides

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5
Q

have a bent shape like in H2O

A

alcohols and ethers

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6
Q

both polar with a 109.5 angle

A

C-O and O-H bonds

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7
Q

alcohols, ethers, and epoxides exhibit

A

dipole-dipole interactions

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8
Q

alcohols are more polar than ethers and epoxides

A

intermolecular hydrogen bonding

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9
Q

affect hydrogen bonding

A

steric factors

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10
Q

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

A

stronger; higher

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11
Q

boiling ponts _______ as the extent of hydrogen bonding _______

A

increase

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12
Q

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

A

soluble

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13
Q

CH3OH
extremely toxic

A

methanol

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14
Q

(CH3)2CHOH
major component of rubbing alcohol

A

2- propanol

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15
Q

HOCH2CH2OH
major component of antifreeze

A

ethylene glycol

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16
Q

yield ethanol and form usable fuels

A

hydrolysis of starch and fermentation

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17
Q

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

A

host-guest complex

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18
Q

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

A

molecular recognition

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19
Q

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

A

nucleophilic substitution reactions

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20
Q

alcohols and ethers are both common products of

A

nucleophilic substitution

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21
Q

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

A

Williamson ether synthesis

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22
Q

para desabotonar un alcohol se necesita una

A

base fuerte

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23
Q

is needed to make an ether

A

alkoxide salt

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24
Q

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

A

halohydrins

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25
Q

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

A

intramolecular

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26
Q

OH is a ___ leaving group

A

very poor

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27
Q

base débil o estable

A

buen grupo saliente

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28
Q

protonates the bad leaving groups and makes them good leaving groups

A

strong acid

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29
Q

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

A

dehydration

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30
Q

more substituted alcohols dehydrate more

A

easily

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31
Q

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

A

regla de zaitsev

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32
Q

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

A

major

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33
Q

react by an E1 mechanism

A

2 and 3 alcohols

34
Q

react by an E2 mechanism

A

1 alcohols

35
Q

E1 mechanism

A
  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
36
Q

E2 mechanism

A
  1. The O atom is protonated
  2. The C-H and C-O bonds are broken and the pi bond is formed
37
Q

favors product formation in dehydration

A

entropy

38
Q

favors reactants

A

enthalpy

39
Q

equilibrium will react to counteract any disturbance to the equilibrium

A

Le chatelier’s principle

40
Q

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

A

right

41
Q

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

A

rearrangement

42
Q

movement of a hydrogen atom

A

1,2-hydride shift

43
Q

movement of an alkyl group

A

1,2- alkyl shift

44
Q

carbocation rearrangement during dehydration

A

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

45
Q

can convert a less stable carbocation into a more stable carbocation

A

1,2 shift

46
Q
  • not unique to dehydration reactions
  • can occur whenever a carbocation is formed as a reactive intermediate
A

rearrangements

47
Q

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

A

rearreglos

48
Q

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

A

substitution reactions

49
Q

mecanismo SN2

A
  1. the O atom is protonated
  2. the C-O bond is broken as the C-Br bond is formed
50
Q

Sn1 mechanism

A
  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)
51
Q

can be converted to alkyl halides using SOCL2 and PBr3

A

primary and 2 alcohols

52
Q

converts alcohols into alkyl chlorides

A

SOCl2 thionyl chloride

53
Q

converts alcohols into alkyl bromides

A

PBr3 phosphorus tribromide

54
Q

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

A

HBr y HI

55
Q

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

A

SN1 mechanism involving a carbocation

56
Q

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

A

SN2 mechanism

57
Q

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

A

epoxides

58
Q

achiral (optically inactive) reactants yield

A

achiral (optically inactive) products

59
Q
  • olefins
  • contain a double bond y su formula general es CnH2n
A

alkenes

60
Q

have the double bond at the end

A

terminal alkenes

61
Q

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

A

internal alkenes

62
Q

contain a double bond in a ring

A

cycloalkenes

63
Q
  • contain a triple bond
  • CnH2n-2
A

alkyne

64
Q

triple bond introduces

A

two degrees of unsaturation

65
Q

terminal alkynes

A

RC—CH

66
Q

internal alkynes

A

RC—CR

67
Q
  • 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
A

alkene hybridization

68
Q
  • 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
A

alkyne bonding

69
Q

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

A

weaker

70
Q

alkenes undergo

A

many reactions that alkanes do not

71
Q

cycloalkanes having fewer than eight carbon atoms have a ___ geometry

A

cis

72
Q

trans alkenes are generally more stable than ____ alkenes

A

cis

73
Q

the rotation around the C-C double bond is

A

restricted

74
Q

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

A

increases

75
Q

has the general structural formula

A

CnH2n acyclic alkene

76
Q

unsaturated hydrocarbons

A

alkenes

77
Q

have the general formula

A

CnH2n cycloalkanes

78
Q

Physical Properties of Alkenes

A
  • 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
79
Q

Physical Properties of Alkynes

A
  • same as alkenes
80
Q

Cis/ trans Differ in Physical Properties

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

Química orgánica 2 (2 decks)

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