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Organic Chemistry > Final Exam > Flashcards

Final Exam Flashcards

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1
Q

Reagent with oxygen bound to oxygen means ____.

A

peroxide

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2
Q

Peroxides are very (stable/unstable)?

A

Unstable

One of the oxygens comes off to form an expoxide at the double bond of the reactant.

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3
Q

What reagents could be used to form

Primary alcohol

Secondary alcohol

Tertiary alcohol

from a terminal pi bond?

A

Primary alcohol: H2SO4, H2O

Secondary alcohol*: Hg(OAc)2

Tertiary alcohol: BH3, THF w/ NaOH, H2O2

*Mercury reagents don’t “rearrange”

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4
Q

Every _______ that breaks gets two _____ per carbon that broke.

A

pi bond; oxygens

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5
Q

When doing ozonolysis, what do you do if:

the oxygen added is terminal

the oxygen added is not terminal

A

the oxygen added is terminal: add “H” to make it an aldehyde

the oxygen added is not terminal: leave it be to make a ketone

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6
Q

Steps for solving:

A
  1. Number C’s starting with aldehyde
  2. The number of pi bonds in reactant will equal half the number of “O” double bonds in product.
  3. Look for how many Carbons are between the two “O” double bonds, and draw a ring structure that corresponds.
  4. Put the pi bond between the two Carbons that had “O” double bonds in the product.
  5. Add any substituents to complete the molecule
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7
Q

Steps to solve:

A
  1. Draw line to divide pi bond.
  2. Draw an “O” on each side of the dividine line.
  3. Draw the product exactly as it looks (except separated)
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8
Q

Which is optically active?

Chiral

Achiral

A

Chiral

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9
Q

An equal mix of R/S configuration

A

Racemic

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10
Q

Identify the molecule as:

Constitutional Isomer

Enantiomer

Diastereomer

A

Diastereomer

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11
Q

Identify the molecule as:

Constitutional Isomer

Enantiomer

Diastereomer

A

Enantiomer

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12
Q

Identify the molecule as:

Constitutional Isomer

Enantiomer

Diastereomer

A

Neither, due to line of symmetry: meso

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13
Q

Catalytic Hydrogenation (Reduction)

syn or anti?

A

syn

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14
Q

Hydrohalogenation

cis or anti?

A

neither: racemic

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15
Q

Will this reaction have a carbocation intermediate?

A

Yes, it is a hydrohalogenation (addition of halogen)

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16
Q

Does a halogenation (addition of two halogens) add

syn or anti?

A

anti

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17
Q

A halohydrin adds

syn or anti?

A

Anti (OH on more subbed side)

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18
Q

This is an example of _____.

A

Halohydrin

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19
Q

3 ways to make a single alkyl halide from alcohol

A
  1. Use haloacid (i.e. HBr)
  2. Use SOCl2
  3. PBr3
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20
Q

1 way to make alkyl halide from ether

A

Use 2 equivalents of haloacid (2HX)

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21
Q

1 way to make an alkyl halide from alkene

A

Haloacid (i.e. HCl)

It breaks the double bond and inserts the halogen in its place

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22
Q

1 way to make vic-dihalide (halogens on adjacent carbons) from alkene

syn or anti addition?

A

Use X2 (i.e. Br2, Cl2) in an organic solvent (i.e. DCM)

anti addition

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23
Q

1 way to form gem-dihalide (two halogens on same carbon) from alkyne

A

2 equivalents of haloacid (i.e. 2HCl)

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24
Q

1 way to make a tetrahalide from alkyne

A

2 equivalents of X2 (i.e. 2Br2)

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25
Q

1 way to make alcohol from alkyl halide

A

use hydroxide (-OH)

26
Q

2 ways to open an epoxide ring

A
  1. Use strong acid (attacks more subbed side)
  2. Use strong nucleophile or base with water (or Nu/H2SO4)…..will attack least subbed side
27
Q

2 Ways to hydrate an alkene

A
  1. Acid catalyzed (Markovnikov): H2O/H2SO4
  2. Hydroboration/oxidation (anti-Mark):
  3. BH3
  4. H2O2/OH

*Markovnikov = add to most subbed side

28
Q

1 way to make ether from alkyl halide

A

alkoxide (RO-)

29
Q

1 way to make an alkoxide from an alcohol

A

NaH

30
Q

How to make an ether from alkene

A

Use an alcohol and sulfuric acid

31
Q

1 way to make a tosylate from alcohol

A

Use TsCl

32
Q

1 way to make an epoxide from a halohydrin (alcohol and halogen)

A

Base (i.e. NaOH)

33
Q

1 way to make an epoxide from alkene

A

mCPBA

34
Q

1 way to make a halohydrin (halogen and alcohol)

A

X2 + H2O

35
Q

1 way to sub “H” for a halogen in alkyl halide (turn an alkyl halide into an alkane)

A

2 Steps

  1. LiAlH4
  2. H2O
36
Q

1 way to reduce an alkyne or alkene to an alkane (syn)

A

Alkene to Alkane

H2
Pd-C (or Lindlar’s catalyst)

Alkyne to Alkane

2H2
Pd-C

37
Q

1 way to make an alkene from a alkyl halide

A

bulky base (i.e. tBuO)

38
Q

2 ways to make an alkene from alcohol

A
  1. H2SO4 (or tosic acid)
  2. POCl3 + pyr.
39
Q

1 way to create alkene from tosylate

A

bulky base

40
Q

______ leaving groups always undergo SN2 reactions, except when reacted with _______. Then, it will be _______.

A

Primary; bulky bases; E2

41
Q

Strong bases (small and large) favor ______ reactions.

A

E2

42
Q

Tertiary leaving groups favor _____ reactions when in protic or aprotic solvents.

A

E1/ SN1

43
Q

SN2 reactions produce _______ products.

A

Inverted

(if you start with R, you end with S)

44
Q

SN1 reactions always produce this type of mixture.

A

Racemic

45
Q

SN1 and E1 reactions can _______, while SN2 and E2 cannot.

A

rearrange

46
Q

Used to make anti-diol

A
  1. RCO3H
  2. H2O (or H+ or OH)
47
Q

2 ways to make a syn-diol

A

1.) KMnO4, H2O, OH

  1. )
  2. OsO4
  3. NaHSO3, H2O
48
Q

1 way to reduce an alkyne, anti

A

Na
NH3(l)

49
Q

2 ways to convert a dihalide to an alkyne

A
  1. ) 2NH2-
  2. ) 2 eq. tBuO in DMSO
50
Q

1 way to make aldehyde from a terminal alkyne

A

Hydroboration/oxidation

  1. ) BH3
  2. ) H2O2/OH-
51
Q

1 way to make an aldehyde that oxidizes a primary alcohol

A

PCC

52
Q

What happens if an internal alkyne is treated with hydroboration/oxidation?

A

It becomes a ketone

53
Q

What happens to a terminal alkyne if it is treated with acid-catalyzed hydration?

A

It becomes a ketone

54
Q

Primary way to oxidize a secondary alcohol

A

Any Cr6+ reagent

(i.e. CrO3 / H2SO4)

55
Q

Oxidizing a secondary alcohol with CrO3/H2SO4 produces ______.

A

ketone

56
Q

This reagent combined with an alkene is called _____.

  1. O3
  2. Zn/H2O or CH3SCH3
A

Oxidative cleavage or ozonolysis

57
Q

Oxidative cleavage (aka ozonolysis) of an alkene produces

A
58
Q

1 way to make a carboxylic acid from an alkyne

A
  1. O3
  2. H2O
59
Q

Oxidation of a primary alcohol by using a strong Cr6+ reageant produces ______.

A

Carboxylic acid

60
Q

1 way to make a carboxylic acid from a primary alcohol

A

Use a strong Cr6+ reagent

61
Q

What does oxidation by using a strong Cr6+ reagent produce when used on the following compounds:

Primary alcohol

Secondary alcohol

A

Primary alcohol: carboxylic acid

Secondary alcohol: ketone

62
Q

What are the products of

A

Organic Chemistry (7 decks)

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