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Organic Chem > chapter 4 > Flashcards

chapter 4 Flashcards

1
Q

functional group

A

the atom or group in a molecule most responsible for the reaction the compound undergoes under a prescribed set of conditions

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2
Q

mechanism

A

how the structure of the reactant is transformed to that ofthe product

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3
Q

conversion of alcohol to alkyl halide

A

R-OH + H-Cl –> R-Cl + H-OH

R is alkyl group

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4
Q

Functional Groups

Class: alcohol

A

ROH
CH3CH2OH
Ethanol

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5
Q

Funtional Groups

Class: alkyl halide

A

RCl
CH3CH2Cl
Chloroethane

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6
Q

Carbonyl group

A

C=O

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7
Q 
Functional class nomenclature
CH3F
A

Methyl fluoride

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8
Q 
Functional class nomenclature
CH3CH2CH2CH2CH2Cl
A

Pentyl chloride

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9
Q

Functional class nomenclature
(CH3CH2)CHCH2CH2CH3
Br

A

1-Ethylbutyl bromide

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10
Q 
Substitutive nomenclature (preferred method)
CH3CH2CH2CH2CH2F
A

1-Fluoropentane

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11
Q

Substitutive nomenclature
CH3CHCH2CH2CH3
Br

A

2-Bromopentane

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12
Q

Substitutive nomenclature
CH3CH2CHCH2CH3
I

A

3-Iodopentane

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13
Q

Functional class Nomenclature of alcohol

A
  • name the alkyl group attached to hydroxyl substituent (-OH)
  • chain is numbered beginning at C to which -OH group is attached
  • add the word alcohol
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14
Q

Substitutive Nomenclature of alcohol

A
  • identify longest C chain that bears the -OH group

- replace -e ending with -ol

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15
Q

determining which direction chains are numbered

A

hydroxyl groups (-OH) outrank alkyl groups and halogen

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16
Q

Primary alcohols and alkyl halides

A

RCH2G
R is alkyl group
G is functional group

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17
Q

Secondary alcohol and alkyl halides

A

R2CHG

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18
Q

Tertiary alcohol and alkyl halide

A

R3CG

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19
Q

C-O and C-H bonds

A

are polar covalent

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20
Q

alcohols and alkyl halides

A

are polar molecules

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21
Q

boiling points of similar size molecules

A

are higher in polar molecules

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22
Q

bp of similar size molecules with hydrogen bonding

A
  • these molecules have dipole-dipole attraction

- OH group of one molecule is hydrogen bond acceptor while -OH group of other molecule is hydrogen bond donor

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23
Q

in organic molecules

A

hydrogen bonding only occurs between OH or NH protons

24
Q

alkyl halides

A

are insoluble in water

25
low-molecular weight alcohols
are soluble in water | -ex. methyl, ethyl, n-propyl, isopropyl
26
higher alcohols
become more hydrocarbon-like and less water soluble
27
hydrogen halides
order of reactivity parallels acidity | HI>HBr>HCl>>HF
28
reactivity for alcohols
- tertiary alcohols are most reactive (converted to alkyl chlorides in minutes) - primary alcohols are least reactive (conversion takes too long)
29
substitution
reaction of an alcohol with a hydrogen halide
30
mechanism
step-by-step pathway of bond cleavage and bond formation that leads from reactants to products
31
mechanism steps
- step 1: proton transfer (protonation=instantaneous) exothermic - step 2: carbocation formation (dissociation=slow) endothermic - step 3: reaction of cation with chloride ion (capture=fast) exothermic
32
Hammond's Postulate
if two states are similar in energy, they are similar in structure
33
electrophilic
- electron loving - electron pair acceptors - react with Lewis bases
34
nucleophiles
- nucleus seekers | - react with electophiles
35
rate-determining step
- a reaction can proceed no faster than its slowest step | - in mechanism it's often 2nd step (dissociation, making of carbocation)
36
Sn1 mechanism
- slowest step is considered to be unimolecular | - first order chemical reaction
37
unimolecular
only one species undergoes a chemical change
38
bimolecular
two molecules undergo a chemical change
39
stability of carbocation
- tertiary cation is most stable | - -because C-C bond is longer than C-H bond, allowing electrons to move easier
40
inductive effect
helps spread the + charge out on the C | -methyl groups (CH3) are better at donating electrons than H is
41
Sn2 | methyl and primary alcohols
secondary order because step 2 is rate determining step - if concentration of 1 compound is doubled, the rate of reaction doubles - if concentration of both compounds is doubled, the rate of reaction is x4
42
2 ways of converting alcohol to alkyl halide
- add HCl to alcohol, cook for sometime, alkyl halide is produced - add thionyl chloride (SOCl2)
43
Reaction rate
tertiary>secondary>primary - governed by the activation energy of the slowest step, regardless of how many steps there are - ex. SN2 reactions are still slower than SN1 even though there are fewer steps
44
Converting alcohol to alkyl halide with thionyl chloride
- requires use of pyridine in order to consume HCl that is produced - used in primary and secondary alkyl chlorides
45
Halogenation of Alkanes
R-H +X2 --> R-X + H-X | CH4 + Cl2 --> CH3Cl + HCl
46
Alkanes to alkyl halides
- in order to make only CCl4 --> Cl2 has to be in excess at the beginning of the reaction - in order to make only CH3Cl --> use excess CH4 and limit Cl2
47
Free radicals
- species that contain unpaired electrons | - neutral and nonpolar
48
homolytic cleavage
the bond between two atoms is broken so that each of them retains one of the electrons in the bond
49
heterolytic cleavage
one fragment of compound retains both electrons
50
chain-terminating steps
- the chain sequence is interrupted due to two odd-electron species combine to give an even-electron product - when radicals combine and go away - less likely to occur than propagation steps
51
bond breaking
- easier to break a secondary H-C bond than it is to break a primary H-C bond - secondary radical is more stable than a primary radical - just like tertiary/secondary carbocations are more stable than primary carbocations
52
halogenation of higher alkanes
- light is used to break Cl2 homolytically | - Cl atom is selective: it chooses secondary H 3.9 times more than primary H
53
relative rate (chloronation) vs relative rate (bromonation)
- chloronation: R3CH>R2CH2>RCH3 (5.2, 3.9, 1) | - bromonation: R3CH>R2CH2>RCH3 (1640, 82, 1)
54
bromine
-can do what chlorine does -but bromine in more selective than chlorine C-Br bond is longer than C-Cl so it cares more about which H to replace -Br abstraction of H is more selective than Cl abstraction of H
55
stability of free radicals
methyl radical

Organic Chem (7 decks)

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