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Organic Chemistry I > Chapter 6: ROH > Flashcards

Chapter 6: ROH Flashcards

(85 cards)

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1
Q

functional group definition

A

structural unit responsible for characteristics, physical and chemical properties under conditions

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2
Q

what are the 2 different naming conventions in IUPAC

A 
functional class
substitutive
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3
Q

what IUPAC naming class is preffered

A

substitutive

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4
Q

main difference between functional class and substitutive names

A 
functional - alkyl followed by "alcohol"
substitutive - start with longest C chain that has the OH group
number closest to OH
replace -ane with -ol
substituents and location BFORE parent
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5
Q

where is OH assumed to be attached in cyclic alcohols

A

C-1

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6
Q

does alcohol or a halogen have higher priority

A

OH has higher priority than halo

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7
Q

how is the C-O bond made in alcohols

A
  • overlap of sp3 orbital on carbon
  • overlaps with one sp3 on oxygen
  • oxygen is left with 2 nonbonding e- pairs
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8
Q

how are bonds made in alkyl halides

A

-halogen is connected to the carbon with a SIGMA bond

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9
Q

carbon-halogen bond distances trend

A

C-F < C-Cl < C-Br < C-I

more electronegetive halogen = smaller bond distance

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10
Q

what type of bonds do alkyl halides and alcohols have

A

polar bonds, and may be polar molecules

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11
Q

dipole-dipole attractive forces

A

molecules with permanent dipoles have a stronger dipole-dipole intermolecular interaction than alkanes

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12
Q

why does flouroethane, for example, have a higher boiling point than propane

A

because its dipole-dipole forces are stronger (flourine is very electronegative) and therefore boiling point is higher

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13
Q

what is different about ethanol and its boiling point

A

ethanols boiling point is so high that dipole-dipole interactions are not enough to explain it

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14
Q

explain bonding in alcohols

A

alcohols have hydrogen bonding (dipole-dipole)

partially positive proton of one -OH group interacts with the partially negative oxygen of a second ethanol

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15
Q

hydrogen bond acceptor and donor in alcohol bonding

A

oxygen = hydrogen bond acceptor

OH hydrogen = hydrogen bond donor

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16
Q

what are the onlu elements involved in hydrogen bonding in organic compounds

A

oxygen
nitrogen

NO

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17
Q

what are alcohols and their hydrogen bonds strong enough to do

A

impose structural order

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18
Q

methyl

A

CH3

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19
Q

ethyl

A

CH3CH2

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20
Q

propyl

A

CH3CH2CH2

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21
Q

pentyl

A

CH3(CH2)3CH2

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22
Q

hexyl

A

CH3(CH2)4CH2

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23
Q

iodine and polarization

A

iodine is highly polarizable

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24
Q

why is iodine highly polarizable

A

because the valence electrons are far from the nucleus

induced dipole-induced dipole forces

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25
connection between halogens, dipoles and boiling point
- increase the number of halogens (Cl, Br, I) - increases the dipoles - increases boiling point
26
flourine and polarization
flourine has very low polarizability, and boiling points do not increase as you increase the amount of flourine
27
solubility of alkyl halides
insoluble in water
28
solubility of alcohols in water
is directly related to the size of the alkyl group that the OH is attached to (the more, the less soluble)
29
alcohols that are totally miscible in water
methyl, ethyl, n-propyl, and isopropyl
30
what is the only amount of octanol that dissolves in water
1 mL 1-octonol in 2000 mL water
31
densities compared to water
less dense than h2O = alkyl flourides and chlorides more dense than water = alkyl bromides and iodides, CH2Cl2
32
halogenation and density
increasing halogenation increases density
33
what are the 3 main steps in radical mechanisms
1. chain initiation 2. chain propagation 3. chain termination
34
what type of arrow do you use in radical mechanisms
fish-hook arrows
35
what are the problems associated with halogenation of alkanes
1. different hydrogens can lead to different products | 2. can get over-halogenation
36
radical stability
methyl < primary < secondary < tertiary
37
synthesis
methods of preparation of alkyl halides
38
mechanism
the step-by-step description of how reactions take place
39
alcohol reaction rate
tertiary alcohols react fastest at low temps primary alcohols react slowest and need the highest temps
40
bimolecular reaction
both reactants change
41
how is the central carbon hybridized in carbocation
sp2 positive charge is in the empty p-orbital
42
characteristic of carbocations
they are electrophilic meaning they seek electrons and love them mean they are lewis acids
43
SN1 nucleophile
is a nonbonding electron pair in a p-orbital that interacts with the empty p-orbital of the carbonation to form a sigma bond
44
in Sn1, what must the sum of each individual step equal
the overall reaction equation
45
what type of reaction is Sn1 and why
substituation reaction nucleophile chloride takes the place of OH
46
what is important about the slow step in Sn1 step 2
unimolecular rate determining step the overall reaction cannot go faster than this step
47
where are the alkyl groups attached to stabilize a carbocation
directly attached to the positively charges carbon
48
how are carbocations defined
methyl, primary, secondary, tertiary depending on how many carbons are directly attached to the cationic carbon
49
stability vs. carbocation type
more stable as it is attached to more carbons least stable is methyl, most is tertiary
50
inductive effect
alkyl groups push electron density onto C+
51
how is the methyl cation in inductive effect
has an intense positive charge
52
the more the charge is delocalized on a cation...
the more stable the cation
53
how are carbocations stabilized
by delocalization of electrons from the sigma bonds, to the + carbon in the empty p orbital
54
what does MO theory predict about bonding orbitals
predicts a bonding orbital with 2 electrons that spans the sigma bond and the positive carbon
55
relationship between formation of carbocation and stability
the rate of formation of the carbocation is related to the stability of the carbocation formed
56
what tracks the stability of the carbocation and why
the transition state is closer in energy to the carbocation so the activation energy tracks the stability of the carbocation
57
what type of reaction is Sn2?
a substitution reaction
58
what is an alkeal
a protonated alcohol
59
why do primary methyls need SN2
because primary methyl carbocations are very unstable, must react in a different way
60
what is thionyl chloride used for in reactions with alcohol
to transform primary and secondary alcohols into alkyl chlorides (not tertiary)
61
what is pyridine used for
it is a base used to neutralize the acid (HCl) formed
62
phosphorus tribromide reacts with what to form what
reacts with alcohols to form alkyl bromides | SN2
63
halogenation of F2
is explosive
64
halogenation of I2
is endothermic
65
halogenation of alkanes and what they are useful for
the reaction is exothermic useful for Cl2 and Br2
66
what are the intermediates in chlorination of methane
free radicals
67
what do free radicals contain
unpaired electrons
68
how do yyou classify radicals
by how many carbons they are directly attached to primary, secondary, tertiary and methyl
69
hybridization of carbon atom with unpaired electron where is the unpaired electron
sp2 unpaired electron is in the 2p orbital
70
what makes free radicals more stable and why
the more alkyl groups connected to the radical, the substituated and the more stable!
71
trend in stability for free radicals
methyl
72
how are radicals produced
bond cleavage
73
how many bonding electrons does each atom have in homolytic bond cleavage
each atom retains one of the bonding electrons
74
what is bond dissociation enthalpy
the energy required for bond to dissociate
75
what happens to bonding electrons in heterolytic cleavage
the more electronegative element retains both bonding electrons
76
how can we quantify radical stability
comparing the energy required for homolytic bond cleavage
77
relationship between stability of radicals and their bond dissociation enthalpies
the less energy, the more stable the radical
78
how are mono halogenation reactions of higher alkanes initiated in lab
you use light (hv)
79
what does cyclobutane yield in monohalogenation of higher alkanes and why
a single monochlorination product because the 8 hydrogens result in the same product being formed
80
relationship between transition state and abstraction of a secondary hydrogen (compared to primary)
the transition state is lower in energy for abstraction of a secondary carbon because a secondary radical is more stable
81
what type of hydrogen does bromination favor
tertiary substitution
82
what type of energy pattern is hydrogen atom abstraction for chlorination
exothermic
83
what type of energy pattern is hydrogen atom abstraction for bromination
endothermic
84
is hydrogen atom abstraction for chlorination or bromination more selective and why
bromination because it is endothermic
85
definition of hydrogen abstraction
removal of an atom or group from a molecule by a RADICAL

Organic Chemistry I (9 decks)

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