Jt 1 A Uhcl Orgo Ii Exam1 Misc

Front 1

Enantiomer

Back 1

1 of 2 stereoisomers that are mirror images of each other that are "non-superposable."

Front 2

Diastereomer

Back 2

When two or more stereoisomers have different configurations at one or more stereocenters & are not mirror images.

Front 3

Meso Structure

Back 3

Compound that is superposable on its mirror image.

Front 4

Name the types of halides....

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methyl halide
1° - primary alkyl halide
2° - secondary alkyl halide
3° - tertiary alkyl halide

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1° - primary alkyl halide...

Back 5

1 alkyl group attached to head carbon

Front 6

2° - secondary alkyl halide

Back 6

2 alkyl group attached to head carbon

Front 7

3° - tertiary alkyl halide

Back 7

3 alkyl group attached to head carbon

Front 8

A nucleophile is...

Back 8

a compound that either is negatively charged or has a region of high electron density(lone pair/double bond).

Front 9

A electrophile is...

Back 9

a compound that either is + charged or has a region of low electron density.

Front 10

SN1 means...

Back 10

substitution nucleophile
unimolecular...

Front 11

SN2 means...

Back 11

substitution nucleophile
bimolecular...

Front 12

SN1/SN2 reactions result in a racemix product mixture.

Back 12

SN1

Front 13

1st degree molecules undergo SN1/SN2.

Back 13

SN2

Front 14

3rd degree molecules undergo SN1/SN2.

Back 14

SN1

Front 15

1st degree molecules undergo SN1/SN2.

Back 15

SN2

Front 16

3rd degree molecules undergo SN1/SN2.

Back 16

SN1

Front 17

Does a strong nucleophile increases the reaction rate of an SN1 reaction?

Back 17

No

Front 18

Does a strong nucleophile increases the reaction rate of an SN2 reaction?

Back 18

Yes

Front 19

Strong nucleophiles favor SN*** reactions.

Back 19

SN2

Front 20

Polar aprotic solvents prefer SN*** reactions.

Back 20

SN2

Front 21

Strong nucleophiles prefer SN*** reactions.

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SN2

Front 22

Weak nucleophiles prefer SN*** reactions.

Back 22

SN1

Front 23

Name some alkane reactions...

Back 23

halogenation
combustion
cracking

Front 24

All Organic Reactions Fall into there categories
1) S***
2) A***
3) E***
4) R***

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1) Substitution
2) Addition
3) Elimination
4) Rearrangement

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*** State: Point on the reaction coordinate when the potential energy is maximum.

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Transition

Front 26

***: A potential energy minimum between two transition states.

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Intermediate

Front 27

Walden *** Reaction

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Inversion

Front 28

***: A species w/unshared electron pair seeking a *** charge.

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Nucleophile
positive

Front 29

A good leaving group must be able to leave as a relatively stable, weakly *** molecule, or i***.

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basic --- ion

Front 30

The SN2 Reaction
• Reaction is with inversion at *** center
• Follows *** order reaction kinetics

Back 30

reacting
second

Front 31

SN2?

Back 31

S - substitution
N - nucleophilic
2 - bimolecular

Front 32

Alkyl halides are polarized at the *** bond, making the carbon ***.

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carbon-halide
electrophilic

Front 33

The study of rates of reactions is called ***.

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kinetics

Front 34

SN# involves a transition state in which both reactants are together.

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2

Front 35

The transition state of an SN2 reaction has a *** arrangement of the carbon atom and the remaining three groups

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planar

Front 36

--- SN2 ---
There is/isn't a reaction at C=C (*** halides).
*** halides are most reactive
*** halides are unreactive by this path

Back 36

isn't --- vinyl
Methyl
Tertiary

Front 37

No SN2 substitution of v*** halides
& a*** halides.

Back 37

vinyl
aryl

Front 38

Better nucleophiles are higher/lower in a column of the periodic table.

Back 38

lower

Front 39

What is a vinylic halide?

Back 39

=CHX

Front 40

*** (Latin = ***) refers to the relationship between 2 groups attached to the same atom.

Back 40

Geminal
twins

Front 41

*** (Latin = ***) stands for any 2 groups bonded to two adjacent carbon atoms

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Vicinal
neighbor

Front 42

--- t-butyl ---
1) The "t" signifies what?
2) Connected where?
3) Butyl?

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1) tertiary(3)
2) first carbon
3) 4 carbons

Front 43

--- sec-butyl ---
1) The "sec" signifies what?
2) Connected where?

Back 43

1) secondary
2) first carbon

Front 44

--- isobutyl ---
1) "iso" signifies what?
2) Connected where?

Back 44

1) equal
2) last carbon

Front 45

--- n-butyl ---
"n" signifies what?

Back 45

normal

Front 46

C-X dipole moments are weird.

What is the strongest"
F, Cl, I or Br?

Back 46

Cl
then F, Br, and I

Front 47

-C≡N is a *** group.
AKA anion CN−

Back 47

cyanide

Front 48

Nitrogen has *** valence electrons available for bonding.

Back 48

five

Front 49

F- is a strong/weak nucleophile.

Back 49

weak

Front 50

Boron and Aluminum need *** valence protons to satisfy their happiness.

Back 50

three

Front 51

Factor favorable for nucleophilicity but NOT basicity.

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polarizability

Front 52

DMF is a nonpolar/polar aprotic/protic solvent w/high BP.

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polar aprotic
Di - methyl - formamide

Front 53

***: special type of SN or E reaction where the nucleophile is also the solvent.

Back 53

Solvolysis

Front 54

Arrange in order of increasing reactivity w/ethanol solvolysis:

t-butyl bromide
t-butyl iodide
isopropyl chloride
methyl iodide

Back 54

methyl iodide <
isopropyl chloride <
t-butyl bromide <
t-butyl iodide

Front 55

List in order of increasing reactivity as substrates in SN1 reactions:
PhBr
PhCH2Br
PhCH(CH3)Br

Back 55

PhBr <
PhCH2Br <
PhCH(CH3)Br

Front 56

SN1 reactions usually proceed with:
A) equal inversion/retention
B) slightly more inversion than retention
C) slightly more retention then inversion
D) complete inversion
E) complete retention

Back 56

B) slightly more inversion than retention

Front 57

When steric configuration doesn't change during a reaction it's said to occur with __________ of its stereochemistry.

Back 57

retention

Front 58

Which describe E1 reactions of alkyl halides (RX)?
I. Rate = k[base]
II. Rate = k[base][RX]
III. Rate = k[RX]
IV. Reactions occur in 2 or more distinct steps.
V. Rearrangements are sometimes seen.

Back 58

III
IV
V

Front 59

Q: Why does CH2=CH-CHBr-CH3 undergo solvolysis more rapidly than 2-bromobutane?
A: The i*** carbocation is stabilized by r***.

Back 59

intermediate
resonance

Front 60

Dehydration of 1-butanol w/acid @ 140°C results in mainly trans-2-butene.... via E# w/a *** shift.

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E1
hydride

Front 61

2) Which of the following is classified as a vinylic halide?
A) CH3CH=CHOH
B) CH3CH=CHCl
C) CH3CH=CHCH2Cl
D) CH3CH2CH2CH2Br
E) BrCH2CH=CH2

Back 61

B) CH3CH=CHCl

Front 62

23) Which of the following compounds will undergo an SN2 reaction most readily?
A) (CH3)3CCH2I
B) (CH3)3CCl
C) (CH3)2CHI
D) (CH3)2CHCH2CH2CH2I
E) (CH3)2CHCH2CH2CH2Cl

Back 62

D) (CH3)2CHCH2CH2CH2I

Front 63

40) Which of the following alkyl bromides undergoes solvolysis in aqueous methanol most rapidly?
A) PhCHBrCH3
B) (CH3)2CHCH2CH2Br
C) (CH3)2CHCH2CHBrCH3
D) CH3CH2CH2CH2Br
E) PhBr

Back 63

A) PhCHBrCH3

Front 64

44) List the following bromides in order of their increasing reactivity as substrates in SN1 reactions: 2-chlorobutane, 2-iodobutane, and 1-iodobutane.

Back 64

Answer: 1-iodobutane < 2-chlorobutane < 2-iodobutane

Front 65

How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination?

Back 65

5

Front 66

When two diastereoisomers differ from each other at only one stereocenter they are ***.

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epimers

Front 67

--- H1 NMR Signals ---
The *** of the signals shows how shielded or deshielded the proton is.

Back 67

location

Front 68

--- H1 NMR Signals ---
The *** of the signal shows the number of protons of that type.

Back 68

intensity

Front 69

--- H1 NMR Signals ---
Signal *** shows the number of protons on adjacent atoms.

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splitting

Front 70

The more shielded methyl protons appear toward the *** of the spectrum (*** field)

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right
higher

Front 71

2,130hz/300,000,000 = # ppm

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7.10

Front 72

More electronegative atoms deshield more and give *** shift values.

Back 72

larger

Front 73

1 delta = 1 ***

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ppm
(same over all frequency NMRs)

Front 74

The chemical shift of an NMR absorption in DELTA units is ***, regardless of the operation frequency of the spectrometer.

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constant

Front 75

DEPT-NMR allows us to determine...

Back 75

# of H attached to each C.

Front 76

Coupling constants are independent/dependent of field strength.

Back 76

independent

Front 77

The coupling constant is the *** between the peaks of a m*** (in Hz).

Back 77

distance
multiplet

Front 78

***topic groups in a chemical compound are equivalent groups.

Back 78

Homo

Front 79

Descriptions of *** are used to describe the stereochemical relationships between substituents... hetero, homo, enantio, or diastereo -topic.

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Topicity

Front 80

*** H+ are chemically & electronically equivalent... but replacement causes chirality.

Back 80

Enantiotopic

Front 81

*** H+ are not chemically & electronically equivalent.

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Diastereotopic

Front 82

Less shielded H+ need *** energy for resonance and are found on the *** of the NMR chart.

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less
left

Front 83

More shielded H+ need *** energy for resonance and are found on the *** of the NMR chart.

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more
right

Front 84

Suffix
-oate?

Back 84

Carboxylate
or
Ester

Front 85

--- NMR ---
Integrating is used to...

Back 85

determine RATIO of H+

Front 86

--- NMR ---
Spin-spin splitting is used to...

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determine # of H+ is ADJACENT carbons
Triplet = 2 adjacent H+

Front 87

Septet?

Back 87

7

Front 88

*** is the process by which an object is exposed to radiation.

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Irradiation

Front 89

Name one factor that is favorable for nucleophilicity but not for basicity.

Back 89

polarizability