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Organic Chemistry MCAT > Nitrogen and Phosphorous Containing Compounds > Flashcards

Nitrogen and Phosphorous Containing Compounds Flashcards

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1
Q

Amino acids contain an what groups?

A

An amino group and a carboxyl group attached to a single carbon (the alpha carbon)

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2
Q

The two other substituents of amino acids are a hydrogen atom and a side chain referred to as the _____________ group

A

R

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3
Q

What is the only amino acid that is NOT CHIRAL?

A

Glycine

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4
Q

All naturally occurring amino acids in euKs, except for glycine, are ________________ active.

A

optically

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5
Q

For amino acids, the Fischer projection for amino acids is drawn with the amino group on the _____________

A

left

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6
Q

L amino acids have the (S) configuration, except for _____________, which is (R) because of the change in priority caused by the sulfur in its R group

A

cysteine

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7
Q

Amino acids, with their acidic carboxyl group and basic amino group, are ___________________ molecules. That is, can act as both acids and bases

A

amphoteric

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8
Q

Amino groups take on the positive charge by being _______________

A

protonated

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9
Q

Carboxyl groups can take the negative charges by being ______________

A

deprotonated

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10
Q

When an amino acid is put into a solution, it will take on both charges, forming a dipolar ion or ___________________

A

zwitterion

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11
Q

What are the five categories of amino acids?

A

Nonpolar aromatic, aromatic, polar negatively charged (acidic), positively charged (basic), and polar

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12
Q

Nonpolar nonaromatic amino acids

A

alanine, valine, leucine, and isoleucine.
Also glycine, proline, and methionine

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13
Q

Aromatic amino acids

A

phenylalanine, tyrosine, tryptophan

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14
Q

Polar amino acids

A

serine, threonine, asparagine, glutamine, cysteine

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15
Q

Positively charged amino acids

A

lysine, arginine, histidine

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16
Q

Negatively charged amino acids

A

aspartate, glutamate

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17
Q

Amino acids undergo ______________ reactions to form peptide bonds

A

condensation

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18
Q

Rotation is limited around the peptide bond. Why?

A

Resonance gives the C-N bond partial double bond character.

19
Q

What makes glycine unique among the amino acids?

A

All amino acids, except glycine, have choral a-carbons. Because the R group of glycine is a hydrogen atom. It is not chiral and there is not optically active.

20
Q

Amino acids are amphoteric. What does this mean? What functional groups give amino acids this characteristic?

A

Can act as an acid or a base

21
Q

How are peptide bonds formed? How are they cleaved?

A

Formed by condensation, cleaved by hydrolysis

22
Q

Why is the C-N bond of an amide planar?

A

The C-N bond of an amide is planar because it has partial double bond character due to resonance. Double bonds exist in a planar conformation and restrict movement.

23
Q

What is Strecker synthesis? (Step 1)

A
  1. Starts with an aldehyde, ammonium chloride (NH4Cl) and potassium cyanide (KCN)
  2. The carbonyl oxygen of aldehyde is protonated, increasing electrophilicity of the carbonyl carbon
  3. Ammonia attacks carbonyl carbon, forming an imine
  4. Imine is susceptible to nucleophilic addition, thus CN- anion from KCN attacks, forming a nitrile (C triple bond N)
  5. The final molecule at the end of step 1 is an aminonitrile, a compound containing an amino group and a nitrile group.
24
Q

What is Strecker synthesis? (Step 2)

A
  1. The nitrile nitrogen is protonated, increasing the electrophilicity of the nitrile carbon
  2. Water molecule attacks, leading to the creation of a molecule with both an imine and hydroxyl moieties on the same carbon
  3. Imine is attacked by another equivalent of water
  4. Carbonyl is formed, kicking off ammonia and creating a carboxylic acid functionality
25
Q

What are the four reactants in the Strecker synthesis of an amino acid?

A

Aldehyde
KCN
Ammonium Chloride
Water

26
Q

What are the reaction types used in Strecker synthesis?

A

Condensation
Nucleophilic addition
Hydrolysis

27
Q

What is Gabriel (malonic-ester) synthesis?

A
  1. Potassium phthalimide is reacted with diethyl bromomalonate (SN2)
  2. Next, the molecule is hydrolyzed with a strong base and heat.
  3. Dicarboxylic acid is decarboxylated through the addition of acid and heat.
28
Q

Like Strecker synthesis, the Gabriel synthesis starts with a _________________ molecule, thus, the final product is a racemic mixture of L- and D amino acids

A

planar

29
Q

In Gabriel synthesis, ___________ is the nucleophile, the secondary carbon is the _______________, and bromine is the ______________ group

A

phthalimide
electrophile
bromine

30
Q

Potassium pthalimide + diethyl bromomalonate produces what?

A

Pthalimidomalonic ester

31
Q

What are the four main reactants in Gabriel synthesis of an amino acid?

A
  1. Potassium phthalimide
  2. Dietyl bromomalonate
  3. Alkyl halide
  4. Water
32
Q

What are the types of reactions types used in Gabriel synthesis?

A

Two SN2 reactions, hydrolysis and decarboxylation

33
Q

Phosphorous is found in _____________ phosphate (Pi), a buffered mixture of hydrogen phosphate (Formula?). and dihydrogen phosphate (Formula?)

A

Inorganic
HPO4 2-
H2PO4-

34
Q

Phosphorous is found in the backbone of _________________________, which uses ___________________ bonds

A

DNA; phosphodiester

35
Q

In the formation of a phosphodiester bond, __________________ is released.

A

Pyrophosphate (PPi, P2O7 4-)

36
Q

The PPi lost in the formation of phosphodiester bonds can be hydrolyzed to two ______________ phosphates

A

inorganic

37
Q

why are phosphate bonds high energy?

A
  • because of large negative charges in adjacent phosphate groups and resonance stabilization of phosphates
38
Q

What are organic phosphates?

A

Carbon-containing compounds that also have phosphate groups.

39
Q

Organic phosphate examples

A

Nucleotide triphosphates (such as ATP or GTP)
DNA

40
Q

Phosphoric acid has ______________ hydrogens, each with a unique ________________

A

3; pKa

41
Q

The wide variety of pKa values in phosphoric acid allows for what?

A

For it to act as a buffer over a large range of pH values

42
Q

What characteristics make inorganic phosphate so useful for energy transfer biologically?

A

What characteristics make inorganic phosphate so useful for energy transfer biologically?

43
Q

What is an organic phosphate?

A

Carbon-containing compounds with phosphate groups.
Examples are ATP and GTP as well as DNA

44
Q

What characteristics of phosphoric acids make them good buffers?

A

The wide variety of pKa values on the hydrogens make them good buffers.

Organic Chemistry MCAT (12 decks)

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