Allt Flashcards

1
Q

What is a Gringard reagent?

A

A magnesium atom added to an alkyl halide, the Mg will insert in between the carbon and halogen. These are great nucleophiles and will react (basic) even with very weak acids.

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2
Q

Draw the base structure of a ketone.

A

See book

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3
Q

Draw the base structure of an aldehyde.

A

see book

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4
Q

Why do aldehydes and ketones undergo only nucleophilic addition reactions?

A

The aldehydes and ketones are attached to a group that is too strong of a base to be eliminated from the compound.

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5
Q

What is the product of a nucleophilic addition of a Grignard reagent with methanal (formaldehyde)? Draw the mechanism.

A

A primary alcohol

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6
Q

What is the product of a nucleophilic addition of a Grignard reagent with an aldehyde other than methanal? Draw the mechanism.

A

A secondary alcohol

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7
Q

What is the product of a nucleophilic addition of a Grignard reagent with a ketone? Draw the mechanism.

A

A tertiary alcohol

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8
Q

What determines a good leaving group of an alkyl halide in a SN2 reaction?

A

Weak bases. Weak bases are stable bases since they don’t share their electrons (they would’ve shared with the proton) easily. Therefore the base is not strongly bonded to the carbon.

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9
Q

What makes a good nucleophile in a SN2 reaction?

A

The stronger the base, the better the nucleophile. Stronger bases have the negative charge on less electronegative atoms (the electrons are not pulled as strongly towards the negative atom, shares their electrons more easily with protons)

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10
Q

What makes a weak base (electronegativity)?

A

Weak bases are strong acids and have their negative charge on a more electronegative atom.

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11
Q

What is the rate mainly controlled by in a Sn2 mechanism?

A

Steric hindrance - nucleophiles with bulky structures cannot easily approach the backside of the carbon, which slows down the rate.

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12
Q

What is the rate mainly controlled by in a Sn1 mechanism?

A

The stability of the carbocation; tertiary carbocations form more easily than secondary and primary (because of better stability) which affects the rate of the reaction.

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13
Q

What does a unimolecular rate-determining step mean? Sn1 or SN2 reaction?

A

Only one molecule is involved in the rate determining step. SN1 reaction.

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14
Q

What does a bimolecular rate-determining step mean? Sn1 or SN2 reaction?

A

Two molecules are involved in the rate determining step. SN2 reaction.

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15
Q

How does the nucleophile affect the rate of a SN2 reaction and why?

A

A better nucleophile is a strong base and therefore shares their electrons more easily with other compounds.

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16
Q

How does the nucleophile affect the rate of a SN2 reaction and why?

A

A better nucleophile is a stronger base (less electronegative) and therefore has a better distribution of electrons, and thus more easily shares their electrons with other compounds.

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17
Q

By what mechanism does pyran and furan rings form?

A

Formation of hemiacetals and hemiketals is the reaction between an alcohol and an aldehyde/ketone. If the reacting groups belong to the same molecule, then a ring structure can form.

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18
Q

By what mechanism does O-glycosidic bonds between monosaccharides form?

A

Acetal and ketal formation: The hemiacetal/hemiketal of one monosaccharide reacts in a condensation reaction with the hydroxide group of another monosaccharide and forms an O-glycosidic bond.

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19
Q

In the second electrophilic addition in the addition of hydrogen halide to an alkyne, what is the product?

A

An alkane.

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20
Q

What is the product of the electrophilic addition of a hydrogen halide to an alkyne?

A

An alkene.

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21
Q

What type of products form in the addition of H+ to an internal alkyne?

A

It forms two type of products of equal amount, because the hydrogen kan with equal ease attach to either one of the sp carbons. (both are attached to R groups instead av hydrogens).

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22
Q

In the addition of water to an alkene, why does the reaction have to be catalyzed by an acid?

A

Because the water itself is too weak of an electrophile and the pi bond cannot on its own attack a hydrogen. Therefore, the acidic hydrogen acts as an electrophile and provides the formation of a carbocation before the water can perform a nucleophilic attack on the charged carbon.

23
Q

What is the product of an acid-catalyzed addition of water to an alkene?

A

An alcohol.

24
Q

What is an enol? Draw the basic structure of an enol.

A

An enol has a double bond between two carbons, and an OH group attached to one of the sp2 carbons.

25
Q

Why is the imine formation acid catalyzed?

A

Because:

  • The double bonded oxygen need to be protonated in order to provide a good electrophile for the amine to perform nucleophilic attack.
  • The OH group need to be protonated to become a good leaving group (H2O is formed).
26
Q

What determines D-stereochemistry? (carbohydrates)

A

The OH group the farthest away from the aldehyde/ketone group is on the right side.

27
Q

What determines L-stereochemistry? (carbohydrates)

A

The OH group the farthest away from the aldehyde/ketone is on the left side.

28
Q

What is an epimer? (carbohydrates)

A

An isomer which has opposite configuration only at one chiral center.

29
Q

Draw the structure of D-glucose

A

See book

30
Q

Draw the structure of D-ribose

A

See book

31
Q

Draw the structure of D-fructose

A

See book

32
Q

Draw the structure of Dihydroxyacetone

A

See book

33
Q

Draw the structure of D-glyceraldehyde

A

See book

34
Q

What is mutarotation? Which bond has to be broken for a sugar do undergo mutarotation?

A

The interconversion between the alpha and beta configuration. The bond between the anomeric carbon and the oxygen on the top right has to be broken.

35
Q

Draw the the cyclization of a hemiacetal.

A

See book

36
Q

Draw the cyclization of a hemiketal

A

See book

37
Q

What is the main classification of polysaccharides based on?

A

The number of non-hydrolyzable basic sugar units (monosaccharides) linked together via hydrolyzable O-glycosidic bonds.

38
Q

What are triacylglycerols? What are their main function? Draw their general structure.

A

Triacylglycerols:

  • storage lipids
  • energy storage
  • they store more energy than sugars, the oxidation releases more energy
  • Long term storage (as opposed to glycogen)
  • nonpolar - can therefore not be present in membranes

General structure: Three fatty acids (unsaturated or saturated) connected via ester bonds to a glycerol

39
Q

Say the three largest classes of membrane lipids. What are their defining traits, respectively?

A

Phospholipids - has phosphate group attached to alcohol group
Glycolipids - has a saccharide attached to alcohol group
Archeabacterial ether lipids - unique, ‘‘double’’ structure with two alcohol groups

40
Q

What are the two subclasses of phosholipids? What kind of lipid are phospholipids?

A

Glycerophospholipids
Sphingo (phospho)lipids

Phospholipids are membrane lipids.

41
Q

What are the two subclasses of glycolipids? What kind of lipid are phospholipids?

A

Galactolipids
Sphingo (glyco)lipids

Glycolipids are membrane lipids.

42
Q

Tell me about Glycerophospholipids.

What kind of classes do they belong to?

What are their general structure?

A

Glycerophospholipids are membrane lipids and phospholipids. They have a phosphate group attached to the alcohol.

Structure: Alcohol group is a glycerol. Two fatty acids + one phosphate group is attached to it. An amino alcohol is connected to the phosphate group.

43
Q

What are the main functions of phospholipids?

A
  • Reservoirs for intracellular messengers (intracellular messenger molecules can be released from them).
  • Anchoring membrane proteins
44
Q

Tell me about Sphingophospholipids.

What kind of classes do they belong to?

What are their general structure?

A

Sphingophospholipids are phospholipids and membrane lipids. They have a phosphate group attached to the alcohol.

Structure: Alcohol group is sphingosine (amino alcohol). One fatty acid and one phosphate group is attached to it. An additional group is attached to the phosphate.

If the additional group is choline or ethanol amine, the sphingophospholipid is a sphingomyelin.

45
Q

Tell me about Galactolipides.

What kind of classes do they belong to?

What are their general structure?

What are the galactolipides called if a sulfate group is attached to the saccharide?

A

They belong to the glycolipids and the membrane lipids.

Structure: Alcohol group is a glycerol. Two fatty acids and a mono/di-saccharide is attached to the glycerol.

If a sulfate group is attached to the saccharide, it is a sulfolipid.

46
Q

What is sphingosine?

A

An amino alcohol.

47
Q

Tell me about Sphingoglycolipids.

What kind of classes do they belong to?

What are their general structure?

A

They belong to the glycolipids (has saccharide attached to alcohol) and the membrane lipids.

Structure: Alcohol group is a sphingosine. One fatty acid is connected to the alcohol, as well as one mono/oligosaccharide.

48
Q

What are the three subclasses of Sphingoglycolipids?

A

Cerebrosides
Globosides
Gangliosides

49
Q

What are the main functions of Sphingoglycolipids?

A

They are recognition sites on cell surfaces, can act like antigens for the immune system.

Determines human blood groups through an additional saccharide attached.

50
Q

What kind of lipid are Sterols?

A

Membrane lipids

51
Q

What is characteristic for sterols? Give an example of sterol.

A

They have a unique structure of 4 fused rings.

They can act as hormone precursors.

Cholesterol.

52
Q

What is the result of the oxidation of a primary alcohol?Draw the mechanism

A

An aldehyde

53
Q

What is the result of the oxidation of a secondary alcohol? Draw the mechanism

A

A ketone.

54
Q

What is the best reagent when oxidating an alcohol to an aldehyde or a ketone?

A

Chromic acid (H2CrO4)