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Organic Chemistry > Final Exam > Flashcards

Final Exam Flashcards

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1
Q

How can you remember which solvent to use with which reactant?

A

Remember that “like dissolves like”.
Polar solvents are best for dissolving polar reactants (such as ions); nonpolar solvents are best for dissolving nonpolar reactants (such as hydrocarbons).

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2
Q

What is a polar solvent?

A

Solvents with large dipole moments (atoms with very different electronegativities are bonded together).
–Ex. Oxygen bound to Hydrogen

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3
Q

What is a non-polar solvent?

A
  • -Lacks partial charges

- -Bonds are between atoms of similar electronegativity

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4
Q

What is a protic solvent?

A

A solvent with O-H or N-H bonds, which allows hydrogen bonding to occur

  • -Decreases the reactivity of nucleophiles
  • -Reactivity of Nu- increases down a column
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5
Q

What is a aprotic solvent?

A

A solvent that lacks O-H or N-H bonds. These solvents cannot hydrogen bond
–Reactivity of Nu- increases up a column

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6
Q

What are some examples of polar aprotic solvents?

A

Acetone, DMF, DMSO,

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7
Q

What are some examples of polar protic solvents?

A

Ammonia, water, methanol, ethanol, acetic acid

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8
Q

Do vinylic halides undergo Sn2?

A

NO

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9
Q

Do phenols and aryl halides undergo Sn1, Sn2, or neither?

A

NEITHER

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10
Q

In reacting with an epoxide, which carbon will a nucleophile attack in acidic solution?

A

The epoxide oxygen will be protonated first and the nucleophile will attack the MORE substituted carbon

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11
Q

In reacting with an epoxide, which carbon will a nucleophile attack in basic solution?

A

The epoxide oxygen will be protonated first and the nucleophile will attack the LESS substituted carbon

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12
Q

What is necessary for a reaction to undergo elimination by the E2 mechanism?

A
  • -A anti-parallel beta hydrogen (the base will go for the lease sterically hindered hydrogen which will produce the most stable double bond)
  • -A strong bulky base
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13
Q

What does it mean when a system is conjugated?

A

A conjugated system has a region of overlapping p-orbitals, bridging the interjacent sigma bonds. They allow a delocalization of pi electrons across all the adjacent aligned p-orbitals. The pi electrons do not belong to a single bond or atom, but rather to a group of atoms.

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14
Q

When is Huckle’s Rule used and what is it?

A

[1] The molecule must be planar
[2] The molecule must be cyclic
[3] Every atom in the ring must be able to participate in delocalizing the electrons by having a p-orbital or an unshared pair of electrons.
[4] Follows the 4n+2 (where n=0,1,2,3,etc) rule for number of pi electrons
–Thus systems with 2,6,10,14,18, etc. pi electrons are considered aromatic

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15
Q

Which factor generally has the largest influence on stability, inductive or resonance effects?

A

Resonance (resonance trumps everything, except when the atom of interest is directly bonded to a large atom. Then surface area delocalizes electron density the most)

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16
Q

When is BH4 used?

A

To convert an aldehyde to a primary alcohol (preferentially attacks the carbonyl group over a double bond)

17
Q

When is LiAlH4 used?

A

To convert a ketone into a secondary alcohol(preferentially attacks the carbonyl group over a double bond)

18
Q

What is the result of a hydroboration-oxidation reacction with an alkene?

A

Anti-markovnikov addition of H and OH

–Syn addition ONLY

19
Q

What is the result of a hydroboration-oxidation reacction with an alkyne?

A

Anti-markovnikov addition of H and OH (however remember that there is tautomerization from the enol to the keto)
–Syn addition ONLY

20
Q

What type of addition happens in a halogenation reaction?

A

Anti-addition

21
Q

What do epoxides ( –CO3H groups) do?

A

Convert alkenes to epoxides (remember mCPBA)

22
Q

What reagents are needed to perform hydration on a terminal alkyne?

A

H2O, H2SO4, HgSO4

the enol is formed first and tautomerizes to the keto

23
Q

What does tautomerization do?

A

It moves the C=C double bond to a C=O double bond (enol to keto)
–Tautomers are constitutional isomers that differ in the location of a double bond and a hydrogen atom. Two tautomers are in equilibrium with each other ( but the more stable keto is favored)

24
Q

What reagents are needed to perform hydration on a internal alkyne?

A

H2O and H2SO4

the enol is formed first and tautomerizes to the keto

25
Q

What are the reagents for hydroboration-oxidation?

A

BH3 (or B2H6), THF, H2O2, -OH

26
Q

What is the result of reacting KMnO4 with a cycloalkene?

A

It adds to OH groups cis to eachother

27
Q

Why would you use OsO4 over KMnO4?

A

If your solvent is organic, OsO4 is soluble in it, whereas KMnO4 is not

28
Q

What is the Nitrogen Rule for mass spectrometry?

A
  • -A compound that contains an odd number of N atoms gives an odd molecular ion number
  • -Conversely, if the compound contains an even number of N atoms it will have an even molecular ion number
29
Q

How do you know if Chlorine is present in a molecule?

A

When the molecular ion consists of two peaks (M and M + 2) in a 3:1 ratio, an alkyl Cl atom is present.

30
Q

How do you know if Bromine is present in a molecule?

A

When the molecular ion consists of two peaks (M and M + 2) in a 1:1 ratio, an alkyl Br atom is present.

31
Q

What are the common molecular weights of the two Chlorine isotopes?

A

Cl-35, and Cl-37 (in a 3:1 ratio respectively)

32
Q

What are the common molecular weights of the two Bromine isotopes?

A

Br-79, Br-81 (in a 1:1 ratio)

33
Q

What does O2 do in a radical reaction?

A

It acts as a radical inhibitor

34
Q

What percentage of product is given through a radical reaction with Chlorine?

A

1:1

35
Q

What percentage of product is given through a radical reaction with Bromine?

A

99:1

36
Q

Which reacts faster in radical reactions, Chlorine or Bromine?

A

Chlorine, because it is non-selective

37
Q

Which hydrogen will Bromine preferentially attack in a radical reaction?

A

The most substituted (or weakest) C-H bond

38
Q

Is a radical reaction with bromine exotherminc or endothermic?

A

ENDOTHERMIC

39
Q

What are the four types of radical reactions?

A
  • -Halogenation (light and/or heat)
  • -Allylic carbon with NBS
  • -Addition to double bonds (anti-Mark.)
  • -Polymerization

Organic Chemistry (6 decks)

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