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Organic Chem > chapter 4 > Flashcards

chapter 4 Flashcards

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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
Q

low-molecular weight alcohols

A

are soluble in water

-ex. methyl, ethyl, n-propyl, isopropyl

26
Q

higher alcohols

A

become more hydrocarbon-like and less water soluble

27
Q

hydrogen halides

A

order of reactivity parallels acidity

HI>HBr>HCl»HF

28
Q

reactivity for alcohols

A
  • tertiary alcohols are most reactive (converted to alkyl chlorides in minutes)
  • primary alcohols are least reactive (conversion takes too long)
29
Q

substitution

A

reaction of an alcohol with a hydrogen halide

30
Q

mechanism

A

step-by-step pathway of bond cleavage and bond formation that leads from reactants to products

31
Q

mechanism steps

A
  • 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
Q

Hammond’s Postulate

A

if two states are similar in energy, they are similar in structure

33
Q

electrophilic

A
  • electron loving
  • electron pair acceptors
  • react with Lewis bases
34
Q

nucleophiles

A
  • nucleus seekers

- react with electophiles

35
Q

rate-determining step

A
  • a reaction can proceed no faster than its slowest step

- in mechanism it’s often 2nd step (dissociation, making of carbocation)

36
Q

Sn1 mechanism

A
  • slowest step is considered to be unimolecular

- first order chemical reaction

37
Q

unimolecular

A

only one species undergoes a chemical change

38
Q

bimolecular

A

two molecules undergo a chemical change

39
Q

stability of carbocation

A
  • tertiary cation is most stable

- -because C-C bond is longer than C-H bond, allowing electrons to move easier

40
Q

inductive effect

A

helps spread the + charge out on the C

-methyl groups (CH3) are better at donating electrons than H is

41
Q

Sn2

methyl and primary alcohols

A

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
Q

2 ways of converting alcohol to alkyl halide

A
  • add HCl to alcohol, cook for sometime, alkyl halide is produced
  • add thionyl chloride (SOCl2)
43
Q

Reaction rate

A

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
Q

Converting alcohol to alkyl halide with thionyl chloride

A
  • requires use of pyridine in order to consume HCl that is produced
  • used in primary and secondary alkyl chlorides
45
Q

Halogenation of Alkanes

A

R-H +X2 –> R-X + H-X

CH4 + Cl2 –> CH3Cl + HCl

46
Q

Alkanes to alkyl halides

A
  • 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
Q

Free radicals

A
  • species that contain unpaired electrons

- neutral and nonpolar

48
Q

homolytic cleavage

A

the bond between two atoms is broken so that each of them retains one of the electrons in the bond

49
Q

heterolytic cleavage

A

one fragment of compound retains both electrons

50
Q

chain-terminating steps

A
  • 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
Q

bond breaking

A
  • 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
Q

halogenation of higher alkanes

A
  • light is used to break Cl2 homolytically

- Cl atom is selective: it chooses secondary H 3.9 times more than primary H

53
Q

relative rate (chloronation) vs relative rate (bromonation)

A
  • chloronation: R3CH>R2CH2>RCH3 (5.2, 3.9, 1)

- bromonation: R3CH>R2CH2>RCH3 (1640, 82, 1)

54
Q

bromine

A

-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
Q

stability of free radicals

A

methyl radical<tertiary radical

-tertiary radical is most stable

Organic Chem (7 decks)

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