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Organic Chemistry > Exam 2 > Flashcards

Exam 2 Flashcards

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1
Q

What is an alkene?

A

Contain one or more Carbon-Carbon double bonds

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2
Q

What is an alkyne?

A

Contain one or more Carbon-Carbon triple bonds

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3
Q

What is an alkene classified as?

A

Unsaturated hydocarbons

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4
Q

What is an alkyne classified as?

A

Unsaturated hydrocarbons

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5
Q

What does sigma form a bond between?

A

Overlapping sp-sp orbitals

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6
Q

What does a side to side overlap between 2p orbitals form?

A

A pi bond

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7
Q

Why do you start a curved arrow on a pi bond?

A

It has the most energy to react because its electrons are stored in unhybridized orbitals

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8
Q

What is the relationship between bond length and sp orbitals?

A

When S character increases, bond length gets shorter because the spherical shape is shorter than that of the elongated P orbital

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9
Q

What is an isomeric alkene?

A

Differ in the position of the double bonds.

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10
Q

What is a constitutional isomer?

A

Molecules with the same molecular formula, but different in atom connectivity.

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11
Q

What are stereoisomers?

A

Compounds with identical connectivity that differ in the spatial arrangement of their atoms.

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12
Q

What is a sterocenter?

A

An atom is a stereocenter when the exchange of 2 bonded groups gives stereoisomers.

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13
Q

What is this substituent group?

A

Vinyl

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14
Q

What is this substituent group?

A

Allyl

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15
Q

What is this substituent group?

A

Isopropenyl

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16
Q

How do you assign the highest priority?

A

Higher priority goes to the substituent group with the highest atomic number. If the atoms are the same, continue moving outward until the first point of difference.

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17
Q

What does E mean?

A

Trans/Opposite sides of the molecule

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18
Q

What does Z mean?

A

Cis/Same side of the molecule

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19
Q

What is an unsaturation number?

A

Gives info on number of rings and/or pi bonds.

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20
Q

Why are aklenes & alkynes unsaturated?

A

They don’t have the max # of hydrones since there is a C-C double or triple bond.

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21
Q

What is the degree of unsaturation?

A

Each ring and/or pi bond reduces number of hydrogens by 2.

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22
Q

What is the equation to determine unsaturation number?

A
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23
Q

Why is an alkene more polar than an alkane?

A

The C-C double bond creates partial negativity.

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24
Q

How does acid strength relate to bond order?

A

single bond < double bond < triple bond

25
Q

Why are trans alkenes more stable?

A

They lack Van der Waal repulsions.

26
Q

How does the number of alkyl substituents at the double bond affect the stability of an alkene?

A

More substituents on the alkene carbon = more stable (hydrogens do not count)

27
Q

Why is the more substituted alkene more stable?

A

Due to hyperconjugation which is when there molecules in the same plane that can overlap their electron clouds that strengths the p orbital.

28
Q

What is Markovnikov’s rule?

A

During an addition of an alkyl halide, the Halogen will always go on the carbon with more substituents (excluding H). The H will always go on the carbon with more H.

29
Q

What are the 2 steps in the mechanism of addition of hydrogen halides to alkenes?

A
  1. High energy pi bond attacks proton
  2. Carbocations are reactive intermediates that attract halogens.
30
Q

Which carbocations are more stable?

A

tertiary > secondary > primary

31
Q

Why are tertiary carbocations more stable?

A

More substituents on the Carbon = more ability to hyper-conjugate

32
Q

What are the types of carbocation rearrangements?

A

-methyl shift
-hydride shift

33
Q

How do you know when carbocation rearrangements happen?

A
  1. A rearrangement almost always occurs when a more stable carbocation can result.
  2. The group that migrates in a carbocation rearrangement comes from a carbon directly attached to the electron-deficient, positively charged carbon of the carbocation.
  3. Hydride migration typically occurs because it gives the more stable carbocation.
34
Q

What is a cataylst?

A

A substance that increases the reaction rate without being consumed.

35
Q

What occurs in a catalytic hydrogenation of alkenes?

A

Break all double bonds and add H2.

36
Q

What are aromatic bonds?

A

Pi bonds in a benzene ring that are less reactive.

37
Q

What is the “modified Markovnikov’s rule”?

A

The carbon of the double bond with fewer substituents becomes bonded to the less electronegative group. The carbon with more substituents becomes bonded to the more electronegative group.

38
Q

Solvents are generally written _____ the arrow.

A

Under

39
Q

Reactants & catalysts are written ______ the arrow.

A

Over

40
Q

What are vicinal dihalides?

A

Halides are connected on carbons right next to each other.

41
Q

The pi bond is electron rich and therefore serves as a ________.

A

Nucleophile

42
Q

In a bromonium ion, which carbon has a partial positive charge? Why?

A

The longer bond between the EN Br and the carbon means it is weaker so the electrons are pulled closer to the Br. There is only a partial positive charge on the more substituted carbon because it is stabilized by hyperconjugation.

43
Q

Why is a bromonium ion and not a carbocation ion formed?

A
  1. Rearrangments are not observed in bromine addition.
  2. Bromonium ions have more covalent bonds than a carbocation and every atom has an octet.
44
Q

What kind of alkene addition reaction is this?

A

Intramolecular reaction

45
Q

What is an enantiomer?

A

When the mirror image of the same molecule is noncongruent (non-overlapping).

46
Q

What is a chiral molecule?

A

One that has a non-superimposable mirror image.

47
Q

What is an asymmetric carbon?

A

A carbon which is bonded to 4 different groups. An asterisk is used to denote asymmetric carbons.

48
Q

A molecule that contains only one asymmetric carbon is _______ _______.

A

Always chiral

49
Q

If 2 molecules are enantiomers, they are also ______.

A

Chiral

50
Q

If the molecule has a plane of symmetry, is it chiral?

A

No

51
Q

If the molecule has an enantiomer (non-super imposable mirror image), is it chiral?

A

Yes

52
Q

If there is only 1 asymmetric carbon, is the molecule chiral?

A

Yes

53
Q

What kind of reaction is this?

A

Ozonolyis reductive workup

54
Q

What kind of reaction is this?

A

Ozonolyis oxidative workup

55
Q

What is a diastereomer?

A

When some chiral centers change their configuration, but not all of them.

56
Q

An acid catalyzed reaction follows what kind of Markovnikov addition?

A

Normal

57
Q

What happens in an intramolecular reaction?

A

The straight chain structure will convert into a cyclo/ring structure.

58
Q

What kind of reaction is this?

A

Oxymercuration-reduction

59
Q

What kind of Markovnikov additions occurs in a hydroboration-oxidation reaction?

A

Anti-Markovnikov

Organic Chemistry (5 decks)

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