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Sample Cardz > ORGANIC 2: OCHEM 1 Review > Flashcards

ORGANIC 2: OCHEM 1 Review Flashcards

1
Q

True or False

If a molecule can resonate, it is more basic.

A

False!

Resonance makes a molecule more stable and therefore more acidic.

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2
Q

Define

Brønsted-Lowry Acid

A

Proton (H+) donor

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3
Q

Define

Brønsted-Lowry Base

A

Proton (H+) acceptor

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4
Q

What species will always be acids?

A
  1. Strong acids (HCl, HBr, HI, H2SO4, H3PO4, etc.)
  2. Uncommon Lewis acids (B.Al.Sn.Fe.Ti. + halogen)
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5
Q

What species will always be bases?

A
  1. Strong bases (NaOH, LiOH, etc.)
  2. Any time an alkali or alkali earth metal is bound to a non-metal. (NaCH3, LiCH3, etc.)
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6
Q

True or False

The stronger the base, the better a leaving group it will be.

A

False!

Weak bases are bad leaving groups.

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7
Q

What are the three requirements for aromaticity?

A
  1. The compound must be cyclic
  2. The compound must be planar
  3. The compound must have a Huckle number of pi electrons
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8
Q
A
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9
Q
A
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10
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11
Q
A
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12
Q
A
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13
Q
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14
Q
A
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15
Q
A

Dissolving metal reduction (Na, NH3, -78°C) cannot be used on terminal alkynes.

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16
Q
A

Dissolving metal reduction (Na, NH3, -78°C) cannot be used on terminal alkynes.

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17
Q
A

Dissolving metal reduction (Na, NH3, -78°C) cannot be used on terminal alkynes.

18
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Aromatic

19
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Non-aromatic

Cyclic rings 8 members and larger are not planar; fails requirement 2 so non-aromatic.

20
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Anti-aromatic

Cyclic, planar, but does not contain a Huckle number of pi electrons

4n + 2 = 4

n = ½ (not a whole number, therefore not Huckle)

21
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Aromatic

Carbanions are considered to be sp2 hybridized.

22
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Aromatic

23
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Non-Aromatic

Cyclic, but not planar due to sp3 oxygens. If the oxygens gave up a lone pair to the pi cloud, there would not be a Huckle number of electrons.

4n + 2 = 8

n = 3/2

Since requirement #2 wasn’t met, the molecule is non-aromatic

24
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Anti-Aromatic

Cyclic, planar, but does not contain a Huckle number of pi electrons

4n + 2 = 4

n = ½

Carbocations are sp2 hybridized

25
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Aromatic

Group 3 elements only make 3 bonds, making them sp2 hybridized with no lone pair

26
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Aromatic

27
Q

Is the molecule shown below aromatic, anti-aromatic, or non-aromatic?

A

Anti-Aromatic

Cyclic, planar, but non-Huckle number of electrons

28
Q

Define

Electron Donating Group (EDG)

A

An atom or group of atoms capable of donating electrons into a pi system.

Generally defined as an electronegative atom containing a lone pair, or an alkyl group.

29
Q

Define

Electron Withdrawing Group (EWG)

A

An atom or group of atoms capable of withdrawing electrons from a pi system.

Generally defined as an atom that is bound to an electronegative atom.

30
Q

True or False

Electron donating groups increase the acidity of a molecule.

A

False.

EDG’s increase the basicity of a molecule as it is providing more electron density, destabilizing the molecule.

31
Q

True or False

Electron withdrawing groups increase the acidity of a molecule.

A

True!

EWG’s increase the acidity of a molecule by spreading electron density out over more of the molecule.

32
Q

Acidity Trends

Hybridization

A

The more s-character an atom has, the more acidic it will be.

(most acidic) sp > sp2 > sp3 (least acidic)

33
Q

Acidity Trends

Electronegativity

A

If comparing two atoms in the same period, the more electronegative atom will be the more acidic atom.

34
Q

Acidity Trends

Size

A

If comparing two atoms in the same column, the larger atom will be the more acidic compound.

35
Q

Acidity Trends

Resonance

A

The compound that can resonate more will be more acidic.

36
Q

Acidity Trends

Inductive Electron Withdrawal

A

The closer an electronegative atom is to the most acidic proton, the more acidic the compound will be.

37
Q

What is the IUPAC priority list?

A
  1. Alcohols
  2. Amines
  3. Alkenes > Alkynes
  4. Everything else
38
Q

What is the common name of the substituent shown below?

What is the systematic name?

A

Common: isopropyl

Systematic: (1-methylethyl)

39
Q

What is the common name of the substituent shown below?

What is the systematic name?

A

Common: sec-butyl

Systematic: (1-methylpropyl)

40
Q

What is the common name of the substituent shown below?

What is the systematic name?

A

Common: tert-pentyl

Systematic: (1,1-dimethylpropyl)

41
Q

What is the common name of the substituent shown below?

What is the systematic name?

A

Common: tert-butyl

Systematic: (1,1-dimethylethyl)

42
Q

When naming a molecule with containing a double bond, triple bond and an amine, what order should these priority groups be placed when naming the parent chain?

A

Alkene - Alkyne - Amine/Alcohol

en-yn-amine/ol

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