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Organic Chemistry > Exam 3 > Flashcards

Exam 3 Flashcards

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1
Q

What happens to axial substituents when you do a chair flip?

A

They become equatorial substituents

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1
Q

What happens to equitorial substituents when you do a chair flip?

A

They become axial substiuents

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2
Q

What happens to up substituents when you do a chair flip?

A

They become down

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3
Q

What happens to down substituents when you do a chair flip?

A

They become up

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4
Q

What kind of substituents are these?

A

Axial Hydrogens

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5
Q

What kind of substituents are these?

A

Equatorial Hydrogens

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6
Q

Which confirmation group is preferred by groups and why?

A

Equatorial because there are no 1,3 diaxial van der waal repulsions

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7
Q

What is a syn addition?

A

Substituents get added to the same side

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8
Q

What is an anti addition?

A

Substituents get added to different sides

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9
Q

What is a substitution with retention of configuration?

A

The leaving group is on the same side as the nucleophile. The asymmetric carbons have the same configuration.

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10
Q

What is substitution with inversion of configuration?

A

Leaving group is on different side than nucleophile. Asymmetric carbons have different configurations

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11
Q

What stereochemistry is the addition of a halogen to an alkene? Why?

A

Anti-addition; When you make a halogen ion, you occupy 1 side of the face so the opposite side is only space available for another addition.

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12
Q

What are stereospecific reactions?

A

Reactions in which different stereoisomers of a starting material give differ stereoisomers of a product

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13
Q

What is the stereochemistry of a hydroboration-oxidation?

A

Syn Addition

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14
Q

What is the stereochemistry of oxymercuration-reduction?

A

Anti addition

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15
Q

What is the stereochemistry of a hydrogenation reaction?

A

Syn addition

16
Q

To be an alcohol, the OH group has to be attached to what?

A

An sp3 carbon

17
Q

What are the intermolecular forces?

A
  1. Van der Waal’s attraction
  2. Polarizability
  3. Permanent Dipoles
  4. Hydrogen bonds
18
Q

What happens to the Van der Waal’s attraction with the surface area of the interacting electron cloud?

A

Van der Waals’s attraction increases with increasing surface area/molar mass

19
Q

What is the relationship between Van Der Waals’s attraction and boiling point?

A

As VDW attraction increases, boiling point increases because the bond is stronger and therefore harder to break

20
Q

What is polarizability?

A

The polarizability of a molecule is a direct measure of how easy it is to create a dipole moment in a molecule

21
Q

What is the relationship between EN and polarizability?

A

The more EN the halogen, the less polarizability and therefore the weaker the VDW attraction

22
Q

What is a hydrogen bond IMF?

A

An attraction between the H on one atom with an unshared electron pair on another

23
Q

What is a protic solvent?

A

An H-bond donor

24
Q

What does it mean if a solvent is a donor?

A

Lewis Base / electron donator

25
Q

What high dielectric constant classifies a molecule as polar?

A

> 15 = polar

26
Q

What is a polar solvent?

A

A polar solvent effectively separates, or shields ions from one another

27
Q

What does the rule like dissolves like mean?

A

Molecules with similar IMFs can break & form new IMFs between the solute and solvent, therefore dissolving in one another

28
Q

When do nucleophilic substitution reactions happen?

A

Occur with primary alkyl halides

29
Q

If you make an alkene as a product, is the reaction substitution or b-elimination?

A

B-elimination

30
Q

What is the a-carbon in a B-elimination reaction?

A

The carbon bonded to the halogen

31
Q

When do B-elimination reactions occur?

A

Occur with tertiary alkyl halides

32
Q

What kind of reactions do secondary alkyl halides undergo?

A

Both substitution & B-elimination

33
Q

Which side does equilibrium favor?

A

Equilibrium favors side with the weaker base

34
Q

What is a Sn2 reacton?

A

Substitution-Nucleophilic-Bimolecular.
A mechanism in which electron-pair donation by a nucleophile to an atom displaces a leaving group from the same atom in a concerted manner (occurs simultaneously)

35
Q

What does bimolecular mean?

A

The rate-limiting step of the reaction involves 2 species

36
Q

Which reaction is faster: Sn2 or Acid-Base?

A

Acid-base reactions occur instantaneously while most nucleophilic substitution reactions are much slower

37
Q

What is a factor that influences the rate of Sn2 reactions?

A

The less branching there is on the alpha carbon and beta carbons, the faster the reaction will go.

Organic Chemistry (5 decks)

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