Brainscape's Knowledge GenomeTM

Browse over 1 million classes created by top students, professors, publishers, and experts.


See full index

Química Orgánica para el MCAT > Oxygen-Containing Compounds > Flashcards

Oxygen-Containing Compounds Flashcards

You may prefer our related Brainscape-certified flashcards:
MCAT flashcards
1
Q

Physical properties of alcohols

A
  • Hydrogen bonding.
  • Higher boiling point than the same compound without the alcohol group.
  • Water soluble as long as molecule does not contain a long hydrophobic region.
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

SN1 reaction with alcohols

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

SN2 reaction with alcohols

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

What factors favor SN1?

A

stable carbocation, tertiary carbon center, protic solvent.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

What factors favor SN2?

A

unstable carbocation, primary carbon center, aprotic (but polar) solvent.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

Describe the strength of the following oxidizing agents: KMnO4, CrO3, and PCC?

A
  • KMnO4 and CrO3 will oxidize primary alcohols to carboxylic acids
  • PCC (Pyridine Chlorochromate) and other weak oxidizing agents will only oxidize a primary alcohol to the aldehyde.
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

Secondary alcohols will always oxidize to what:

A

Ketones

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

Mechanism of Pinacol Rearrangement

A

A strong acid (H2SO4) protonates and then rearrangement occurs.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

Protection of alcohol groups

A

Best protection group is trimseyl silyl:

  • To protect, add Cl-SiMe3 to R-OH.
  • The alcohol gets “capped” into R-O-SiMe3.
  • To deprotect, add F-.
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

Reactions with SOCl2 and PBr3

A

R-OH + SOCl2 –> R-Cl (by products: SO2 + HCl)

R-OH + PBr3 –> R-Br (by products: H3PO3, R3PO3, HBr)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

Preparation of mesylates, tosylates, and tosylates:

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

Purpose of preparing mesylates, tosylates, and triflates

A

They are great leaving groups for nucleophilic substitution

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

Esterification of alcohol

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

What is an inorganic ester?

A

replace the carbon of esters with a different atoms

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

Formation of inorganic ester using PBr3

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

Formation of an inorganic ester using SOCl2

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

Why are inorganic esters important for biochemistry?

A

In biochemistry DNA/RNA polymerization, the 3’-OH alcohol group attacks the 5’-phosphate to form an inorganic ester linkage (phosphodiester linkage of DNA/RNA backbone).

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
18
Q

Hydrogen bonding of alcohols results in:

A

hydrogen bonding in alcohols give them a higher boiling point than their corresponding alkanes.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

Effect of chain branching on physical properties of alcohols

A

going from straight chain to branched alkane (with same # carbons) = higher freezing/melting point, lower boiling point.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

Physical properties of aldehydes and ketones

A
  • C=O bond is polar, with the carbon partially positive and oxygen partially negative.
  • Dipole-dipole interactions give these molecules higher boiling points than their corresponding alkanes, but not as high as the corresponding alcohols or carboxylic acids.
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
21
Q

Nucleophilic addition at the carbonyl bond to form a hemiacetal or acetal.

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
22
Q

Nucelophilic addition at the carbonyl to form an imine

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
23
Q

Nucleophilic addition at the carbonyl to form an enamine

A
24
Q

Halform reaction mechanism

A
25
Q

Aldol condensation mechanism

A
26
Q

Internal H-bonding in 1,3 di-carbonyls

A
27
Q

Keto-Enol Tautomerism (extra: which is more stable?)

A
28
Q

Formation of organometallic compounds and purpose of organometalic compounds

A

Organometallic compounds makes R-, which attacks C=O to make R-C-OH.

The purpose of organometallic compounds is to make carbon-carbon bonds.

29
Q

Wolff-Kishner Reaction

A
30
Q

Grignard Reagents for carbonyls

A

Grignard reagents are just like organometallic reagents, they produce R-.

31
Q

Effect of substituents on reactivity of C=O

A

bulky groups on either side of C=O blocks access to the electrophilic carbon, so reactivity goes down.

32
Q

Why are alpha protons acidic?

A

Alpha proton is acidic because the resulting carbanion is stabilized by resonance.

33
Q

Physical properties and solubility of carboxylic acids

A
  • High boiling point due to hydrogen bonding.
  • Soluble in water.
34
Q

Describe the general mechanism for a nucleophilic attack for a carboxylic attack.

A
35
Q

What is the product of LiAlH4 and a carboxylic acid?

A

It creates a primary alcohol. Carboxylic acids can only be reduced by lithium aluminum hydride.

36
Q

Decarboxylation mechanism for beta-keto acids

A
37
Q

Reactants and mechanism for esterification

A

Carboxylic acid and R-OH in acidic conditions

38
Q

Halogenation of Carboxylic Acids at the alpha position (four-step mechanism)

A
39
Q

General principles of carboxylic acids

A
  • High boiling points due to hydrogen bonding
  • Dimerization due to hydrogen bonding
  • Weak acid
40
Q

Electron Withdrawing Groups Inductive Effect on Carboxylic Acids

A

electron withdrawing groups makes the acid stronger.

41
Q

Physical properties of carboxylic acid derivatives

A
  • C=O bond is polar, so there are dipole-dipole interactions.
  • No hydrogen bond exists in acid chlorides, anhydrides, or esters unless there is an -OH group somewhere.
  • Amides can hydrogen bond because of the N-H group. In fact, hydrogen bonding involving the amide backbone of polypeptides form the secondary structure of proteins.
  • Amides have higher boiling points than the other acid derivatives.
  • Acid derivatives have high boiling points than alkanes because of the C=O dipole interactions.
42
Q

Synthesis of acyl chloride from carboxylic acid

A
43
Q

Reactions of acyl chloride

A
44
Q

Reactions of acid anhydrides

A
45
Q

Reactions of esters

A
46
Q

Amide to carboxylic acid

A
47
Q

Reaction of carboxylic acids to acid derivatives

A
48
Q

Nucleophilic substitution mechanism for carboxylic acids

A
49
Q

Hoffman Rearrangement

A
50
Q

Transesterification reaction

A
51
Q

Hydrolysis of fats and glycerides (saponification)

A
52
Q

Hydrolysis of amides

A
53
Q

Relative reactivity of acid derivatives

A
54
Q

Steric Effects on Carboxylic Acid Derivatives

A

bulky groups around the C=O group helps protect the carbon center from nucleophilic attack.

55
Q

Strain of amides (beta-lactam)

A

Amides have a double bond characteristic between the carbon and nitrogen. This means that the C-N bond can not rotate.

An example is beta-lactam, which is a four-membered ring with 1 amide in it.

Química Orgánica para el MCAT (9 decks)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2024 Bold Learning Solutions. Terms and Conditions