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Z - Chem 2210 (S&T) > Chapters 5-7 > Flashcards

Chapters 5-7 Flashcards

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1
Q

Define isomers

A

same molecular formula

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2
Q

Define constitutional isomers

A

same molecular formula, but different atom connectivity

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3
Q

Define stereoisomers

A

same molecular formula, but a different arrangement of atoms/groups in space

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4
Q

Define diastereomers

A

stereoisomers that are not mirror images

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5
Q

Define enantiomers

A

stereoisomers are non-superimposable mirror images

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6
Q

What is the chiraliy on a pair of enantiomers?

A

they have opposite configurations on all of the chiral centers

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7
Q

What is the symmetry for chiral and achiral molecules?

A

Chiral molecules lack a plane of symmetry

Achiral molecules have at least one plane of symmetry

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8
Q

What are the basic guidlines for the nomenclature of enantiomers?

A

Assign first priority numbers to groups or atoms attached to the chiral centers
Priority numbers are given based on the atomic numbers
(1=highest, 4-=lowest)
If your #4 points back, you are ready to trace the path from 1 to 2 to 3
If that path is clockwise, it is R
If that path is counterclockwise, it is S
Each R or S is for each chiral center, not the entire molecule

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9
Q

What happens when you are assigning priority numbers for the nomenclature of enantiomers and the atom connected to the carbon is the same?

A

If the atom is the same, keep moving to the next one connected to it

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10
Q

What happens when you are assigning priority numbers for the nomenclature of enantiomers and you encounter a multiple bond?

A

They are treated as equal numbers of single bonded atoms
If you have a C=C, break it into two single -C bonds on each carbon

Ex:If you have an aldehyde, make carbon have two single bonds to oxygen, and oxygen have two single bonds to carbon

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11
Q

When happens when you are assigning priority numbers and your #4 is not pointing back?

A 
You need to do two group exchanges to make it go back
Two exchanges (on the same chiral center) creates an identical molecule
One would create the enantiomer
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12
Q

How do you know the maximum number of stereoisomers for compounds with more than one chiral center?

A 
the maximum (can be fewer) number of stereoisomers is equal to 2^n
N is equal to the number of chiral centers
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13
Q

Define meso compounds

A

These have two or more chiral centers, and at least one plane of symmetry

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14
Q

Relate meso compounds to chirality

A

All meso compounds/molecules are achiral (plane), but not all achiral are meso

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15
Q

Describe fischer projections

A

Representations of the molecules in 2D
Whatever is horizontal points toward you
Whatever is vertical is pointing back

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16
Q

What are the general properties of enantiomers?

A

They have the same physical properties (mp, bp, etc)
They rotate the plane of polarized light by the same extent in different directions
They also have vastly different biological properties

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17
Q

Relate chirality to optically active/inactive

A

All chiral molecules are optically active

All achiral molecules are optically inactive

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18
Q

Explain the equation [a]D25 = 1/LC

A

A is the angle of rotation
C is the concentration of the chiral solution
L is the length of tube
The whole thing is called the specific rotation

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19
Q

Define dextrorotatory and levorotatory

A

Dextrorotatory = positive rotation (rotate to the right)
Levorotatory= negative rotation (rotate to the left)
The +/- has nothing to do with R/S

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20
Q

Define racemic mixture

A

An equimolar mixture of two enantiomers will be optically inactive, because they will cancel each other out

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21
Q

Describe the general properties of diastereomers

A

these do not have the same physical properties

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22
Q

How do you determine stereoisomerism in cyclic molecules?

A

ring flips mean that it is safe to assume that is is flat when you are looking for a plane of symmetry . When you are drawing it flat, make sure you keep the cis-trans properties.

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23
Q

What is thermodynamics about?

A

where the equilibrium is

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24
Q

What is kinetics about?

A

how fast the reaction takes place

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25
Q

Define ‘mechanism’

A

a sequence of steps going from the reactants to the products

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26
Q

Define ‘ionic reactions’

A

Involve ions or species with partial charges

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27
Q

Define ‘radical reactions’

A

Involve radicals (species with unpaired electrons)

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28
Q

Define ‘pericyclic reactions’

A

Have a cyclic transition state

Do not involve ions or radicals

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29
Q

If you wanted to break a halogen bond, which halogen would be easiest?

A

The larger the halogen, the longer the bond, and the easier it is to break

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30
Q

Describe nucleophiles, include charges

A

Nucleophiles
Love positive centers
Have an unshared pair of electrons or a negative charge
Can be anionic or neutral

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31
Q

Describe electrophiles, include charges

A 
Electrophile
Loves electrons
Has a positive charge or a partial positive charge
May have a polar covalent bond
Ex: Carbonyl groups
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32
Q

Describe leaving groups and their general characteristics

A

Leaving groups
In this case, the halogen that gets displaced in a nucleophilic substitution
The substituent must be able to leave as a relatively stable, weakly basic molecule or ion

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33
Q

What is special about OTs and OMs?

A

-OTs and -OMs have many resonance structures, so they are more stable as leaving groups

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34
Q

Describe alkyl halides (or haloalkanes)

A

Carbon is sp3

Can be 1, 2, or 3*

35
Q

Describe vinyl halides

A

Carbon is sp2, due to the double bond

36
Q

Describe aryl halides

A

Carbon is sp2, due to the presence of a benzene or other aromatic ring

37
Q

Describe acetylenic halides (or alkynyl halides)

A

Carbon is sp, due to the triple bond

38
Q

Which type of halide will undergo nucleophilic subsitutions and elimination reactions? Why?

A

Alkyl halides will undergo nucleophilic substitutions and elimination reactions, the others will not
They have sp2 or sp, and the nucleophile cannot approach as well

39
Q

Describe how SN2 reactions get their name

A

Sn2 has a bimolecular rate determining step

Second order reaction, Rate=k[nucleophile][substrate]

40
Q

Describe the process of an SN2 reaction

A

Nucleophile attacks on the opposite side to the halogen
Halogen departs on the opposite side to where the nucleophile attacks
The configuration of the stereocenter on the carbon inverts
If it has a chirality center that is R, it will become S and vice versa

41
Q

What kind of nucleophiles do SN2 reactions need (3 characteristics)?

A

strong, small, polarizable

42
Q

Describe how SN1 reactions get their name

A

has a unimolecular rate determining step

Rate depends only on the concentration of the alkyl halide (Rate=k1[RX])

43
Q

Describe the process of an SN1 reaction

A

Will have several, typically 3 steps
Breaking C-X bond (ionization of alkyl halide)
Attaching the nucleophile to the carbocation
Making it neutral

44
Q

Describe the free energy diagram of an SN1 reaction

A

Three hills, corresponding to each transition state
Each hill is smaller than the next
Two valleys, corresponding to the two intermediates
The jumps from each valley to the next hill is much smaller in the 2nd and 3rd step

45
Q

Describe the involvement of stereochemistry in an SN1 reaction

A

The trigonal planar molecule formed by the first step can be attacked from either side
This will form either an R or S compound
If the products do not have a chirality center, they will be the same

46
Q

What kind of nucleophiles do SN1 reactions want?

A

weaker

47
Q

What types of substrates will undergo SN1 reactions? Why?

A

3* and 2* alkyl halides, The more stable the carbocation formed, the faster the reaction, You are more stable when you have electron donating groups (like R)

48
Q

What types of substrates will undergo SN2 reactions? Why?

A

Methyl, 1, and 2 alkyl halides because R groups are blocking the nucleophile from coming in to replace the X

49
Q

Describe how nucleophilcity is determined in SN2 reactions

A

Nucleophilicity is measured in terms of the relative rate of its Sn2 reaction
When the nucleophilic atom is the same, it parallels basicities
A good base is usually a good Nu- (unless they are bulky) because both are donating electrons
When the nucleophilic atom is different, it depends on the solvent

50
Q

What kind of solvents do SN1 reactions like? Why?

A

Polar protic solvents will stabilize the development of the polar transition state
It stabilizes both the positive and negative sections

51
Q

What kind of solvents to SN2 reactions like? Why? Give two examples.

A

The best solvents are polar aprotic (strong dipoles, but without OH or NH)
Ex: DMSO, DMF
They tend to solvate the metal cation the nucleophilic anion is attached to, making the electron pair more available and the approach to the substrate easier

52
Q

For reactions in aprotic solvents, how do you determine nucleophilicity? Why?

A

In aprotic solvents, nucleophilicity parallels basicity (F>Cl>Br>I) because only the cations are solvated. F is smaller in size (so has a large charge per surface area) =stronger

53
Q

For SN2 reactions in protic solvents, how do you determine nucleophilicity? Why?

A

In protic solvents, nucleophilicity goes I>Br>Cl>F because it follows the level of solvation
The smaller the atom, the more solvated it is

54
Q

What are some (3) characteristics of good leaving groups?

A

Small neutral molecules
Those with a lot of resonance
Larger negative molecules (disperse the charge)

55
Q

Describe how you will name alkenes as E and Z

A

Examine the 2 groups or atoms attached to each C of the double bond and decide which has higher priority based on the rules used for R and S nomenclature.
Look at each C separately, and choose one from each C
If the highest priority groups are on the same side, it is Z
If the highest priority groups are on different sides, it is E

56
Q

Describe how the stability of alkenes is determined

A

The more highly subsituted the alkene is, the more stable it is
tetra-substituted>tri->trans-di>cis-di>mono->unsubstituted

57
Q

Describe the substrate used for dehydrohalogenation reactions

A

Any alkyl halide, you remove an X and a H from an adjacent carbon

58
Q

Describe the mechanism of dehydrohalogenation

A

Because you are removing an acid, this only occurs with a strong base (OH-, RO-, H-, NH2-, or C-)
This is a one-step reaction, like Sn2, but with an elimination instead of a substitution
The base grabs the H, and the electrons move to the C-C bond, which kicks out the X
The products are BH, an alkene, and X-
The rate is k[base][substrate]
This is called an E2 reaction

59
Q

Describe how the two reactants in dehydrohalogenation interact

A

The base has a lone pair, and so does the X, so it needs to come from the opposite side, as in Sn2 reactions
The difference is that the base is attacking the H, not a C
The H and X should be anti coplanar for a fast reaction

60
Q

Describe the substrate used for dehydration reactions

A

An alcohol, you remove an OH and a H from an adjacent carbon

61
Q

Describe the mechanism of dehydration

A

The first step is to add an strong acid, like H2SO4 or H3PO4
This will protonate the O from the OH, to form water, a good leaving group
The delta plus on the acid H goes to the lone pair on the oxygen
In the next step, the negative ion leftover from the acid grabs the H to form the double bond
This will give you your acid back, so the acid acts as a catalyst

62
Q

How does the speed of a dehydration reaction vary with the type of substrate?

A

The speed of reaction with a certain alcohol goes R3COH(3)>R2CHOH (2)>RCH2OH (1*)
You could say that you are forming the most stable alkene (highest number of substituents) or that your RDS forms a more stable carbocation (3>2>1, donate e-)

63
Q

Describe how carbocations can rearrange themselves

A

These are called 1,2-shifts of either hydrogen or alkyl groups
Whenever you are working with a cyclic carbocation, make sure that your rearrangement is the most stable both in terms of 3/2/1 prime and in terms of the highest ring (7+ are less stable)
Also make sure that whatever you are doing actually moves the positive charge

64
Q

What kinds (2) of bases will E2 reactions tolerate that substitution reactions will not?

A

Bulky, non-polar/weakly polar

65
Q

What kind of reactant is needed for an E1 reaction that does not occur with a dehydration?

A

a neutral nucleophile

66
Q

What solvents do E1 and E2 reactions like?

A

polar protic (stablize carbocation) and polar aprotic (solvate cation, if any)

67
Q

Compare the temperatures preferred by substitution or elimination reactions

A

Elimination reactions do not mind really high temperatures

68
Q

If an E2 reaction could make two products, how you decide which is the major?

A

choose more substituted unless working with (CH3)3COK

69
Q

Describe the synthesis of alkynes from vicinal dihalides

A

Two halogens on adjacent carbons

Do a double dehydrohalogenation (two E2 reactions)

70
Q

Describe the synthesis of alkynes from genimal dihalides

A

Two halogens on the same carbon

Do a double dehydrohalogenation (two E2 reactions)

71
Q

Describe the hydrogenation of alkenes with either option of reactant

A

Add H2 in the presence of a metal catalyst (such as Pt, Pd, Ni, or Ru)
This is a syn-addition as both hydrogens are delivered on the same side
If the same reaction happens with D2, you will have the exact same product, except D replaces the H

72
Q

Describe the hydrogenation of an alkyne into an alkane

A

Use two H2 instead of one, with the same metal catalysts (Pt, Pd, Ni, Ru)

73
Q

Describe how you would hydrogenate an alkyne into a cis alkene

A

Use the same mechanism (RC≡CR + H2), but use a less reactive catalyst such as Pd/CaCO3 or Ni2B/CaCO3

74
Q

Describe how you would hydrogenate an alkyne into trans

A

Add Na/Li and NH3/EtNH2 to RC≡CR

75
Q

Describe how you would transform a terminal alkyne into a regular alkyne

A

Use NaNH2 then CH3Br, twice
The NaNH2 will rip off a hydrogen, leaving a carbon that is triple bonded with a lone pair
The CH3Br will add back a CH3 to the lone pair

76
Q

If you have hydrogen and a catalyst, what kinds of reactions will take place in a hydrogenation?

A

A H2 and a catalyst is always a syn addition

77
Q

Order the following compounds in order from highest to lowest acidity (or lowest to highest basicity of their conjugates): H-OH, H-OR, H-NH2, , H-C(triple bond)CR , H-CH=CH2, H-CH2CH3

A 
H-OH
H-OR
H-C(triple bond)CR
H-NH2
H-CH=CH2
H-CH2CH3
78
Q

What is the role of NaNH2 as a reactant?

A

If a terminal triple bond is present, it will remove the hydrogen from the end carbon, leaving behind a lone pair of electrons

If a halogen is present, it will remove the halogen and an hydrogen, increasing the bond number by one (ex: turn a single bond into a double bond)

79
Q

What is the role of CH3Br as a reactant in a reaction?

A

If a lone pair is present, it will add a CH3 there

80
Q

What is the role of CH3CH2Br as a reactant in a reaction?

A

If a lone pair is present, it will add a CH3CH2 there

81
Q

What is the role of secondary or tertary halides as a reactant in a reaction?

A

If larger molecules, such as R2CHX are used, you will get RC≡CH and R=CHR (or R=CR2, for a tertiary alkyl halide

82
Q

What is the role of Li/NH3 as a reactant in a reaction?

A

This will turn an RC≡CR into a trans RHC=CHR

83
Q

What is the role of H2/Pd/CaCO3 as a reactant in a reaction?

A

This will turn an alkyne into a cis alkene

84
Q

What is the role of H2/Pd as a reactant in a reaction?

A

This will turn an alkyne/alkene into an alkane

Z - Chem 2210 (S&T) (14 decks)

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