Ochem Exam 2 Flashcards

(36 cards)

1
Q

A molecule with 0 chiral centers is…
A molecule with 1 chiral center is…

A

0 - achiral
1 - chiral

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2
Q

If a molecule’s chiral centers are all the same configuration, then it is a…

A

identical molecule

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3
Q

Can a molecule with 1 chiral center have a diastereomer? Why or why not?

A

No, because if the R/S stays the same it is identical, but if the single R/S changes it is is an enantiomer because “all” the R/S changed.

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4
Q

If a molecule has multiple chiral centers but is overall symmetric, it is a…

A

meso compound

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5
Q

In a molecule with multiple chiral centers, when all the R/S stay the same then the molecules are…

A

identical

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6
Q

In a molecule with multiple chiral centers, when all the R/S change then the molecules are…

A

enantiomers

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7
Q

In a molecule with multiple chiral centers, when only some of the R/S change then the molecules are…

A

diastereomers

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8
Q

Achiral molecules have a —— mirror image.

A

superimposable

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9
Q

Chiral molecules have a ——- mirror image.

A

non superimposable

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10
Q

What is a chiral center?

A

a carbon with 4 different groups

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11
Q

What are the differences in properties between enantiomers and diastereomers?

A

enantiomers: some properties except how they interact with chiral things
diastereomers: different properties

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12
Q

What is a racemic mixture?

A

50/50 mix of enantiomers

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13
Q

When the 4th group is in the back, what direction are the R and S configurations?

A

clockwise - R
counterclockwise - S

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14
Q

When the 4th group is in the front, what direction are the R and S configurations?

A

clockwise - S
counterclockwise - R

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15
Q

When you prioritize groups for chiral center configurations, how do you name them?

A

highest atomic number gets highest priority
if the atom is the same, move out to the first point of difference

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16
Q

What bonds are formed and broken in each of the types of reactions?

A

substitution - break sigma and form sigma
elimination - break 2 sigma and form a pi
addition - break a pi bond and form 2 sigma

17
Q

What do the thermodynamics and kinetics tell you about a reacation?

A

thermodynamics - equilibria/extent/stability
kinetics - rate/speef

18
Q

What does the Keq tell you about a reaction?

A

> 1 product favored (exo)
<1 reactant favored (endo)

19
Q

What does the dH or dG tell you about a reaction?

A
  • product favored (exo)
    + reactant favored (endo)
20
Q

How do you write the rate equation for a reaction?
SN1 and SN2 specifically

A

rate=k[reactants of the rate determining step]
SN1 - rate=k[substrate]
SN2 - rate=k[substrate][nucleophile]

21
Q

The rate determining step is the step with the…

A

highest transition state

22
Q

How does activation energy affect the rate of a reaction? How is activation energy affected by catalyst and temperature?

A

higher Ea = slower
lower Ea = faster

higher temp lowers Ea and increases rate
lower temp increases Ea and slows the rate

23
Q

SN1 has (1/2) step(s) and (does/does not) have an intermediate

A

2 step, does have an intermediate

24
Q

SN2 has (1/2) step(s) and (does/does not) have an intermediate

A

1 step, does not have an intermediate

25
What types of substrate are preferred by SN1 and SN2? Why?
SN1 - tertiary, secondary, and primary if it has resonance. Carbocation needs stabilized by the branches. SN2 - primary, secondary, NEVER tertiary. Needs room for the "backside approach" to happen.
26
How many structures can be produced from an SN1 reaction? Why?
2, because the Nu can bond at the front or back of the carbocation
27
In an SN1 reaction, what happens if the 2 structures produced are enantiomers vs diastereomers?
enantiomers - 50/50 racemic mixture diastereomers - some other mix
28
What makes a good leaving group?
weak base, pKa less than 16 (generally I-, Br-, Cl-, but NOT F-)
29
What type of nucleophile is best for a SN1 and SN2 reaction?
SN1 - must be weak, pKa <4.8, as strong/stronger acid form than carboxylic acid (such as O- halogens-, OAc-, acetic acid OO-) SN2 - good nucleophile, pKa>5 (higher than carboxylic acid)
30
What type of solvent is preferred by SN1 and SN2?
SN1 - polar protic (contain an OH) SN2 - polar aprotic
31
When does inversion occur in an SN2 reaction?
when the backside approach happens on a chiral center
32
For any elimination reaction to happen, there MUST be...
beta hydrogens
33
In an elimination reaction, multiple structures called -------- can be produced if...
regioisomers the beta hydrogens are not equivalent
34
In an elimination reaction, identical beta hydrogens will produce...
identical products
35
tetrasubstituted alkenes are ----- stable than monosubstituted/not substituted alkenes. Why?
more More R groups (increased substitution) means more electrons are donated to the double bond area, so it becomes more stable.
36
Are cis or trans substituted alkenes more stable? Why?
trans, because the groups are farther apart from eachother