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MCAT Ochem Flashcards

0
Q

How do you number a branched chanin?

A

Number it so the most substituents get the lowest number.

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1
Q

In a branched alkane, which chain is the name based on?

A

The longest chain. If two chains are equal length, then the more substituted chain.

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2
Q

What is the shape for neopentyl, sec-butyl and isobuty?

A

Neo:
C
C-C-C-
C

Sec:
C-C-C-
C

Iso:
C-C-C-
C

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3
Q

Which words are considered in the alphabetical order of naming an alkane? Which are ignored?

A

Nonhyphenated roots are considered for the alphabetical order, such as iso-, neo-, cyclo-, etc.

Numerical and hyphenated prefixes are ignored, such as di-, tri-, tert-, sec-

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4
Q

Where are rings numbered from?

A

The ring is numbered starting at the point of greatest substitution.

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5
Q

What is the rule for numbering more complicated molecules?

A
  1. Carbon chain with highest priority functional group is the chain that is numbered
  2. The highest priority group must have as low of a number as possible
  3. Compound name ends with the suffix of that priority group
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6
Q

Who gets preference in a numbering tie between alkenes, alkanes, and alkynes?

A

Alkenes.

Alkanes are lowest on the list.

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7
Q

If an alkyne and alkene are both on a molecule, how is it named?

A

y-root-en-x-yne

y = position of double bond
x = position of triple bond
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8
Q

What are common names for the following:

  1. 3-bromo-1-propene
  2. chloroethene
A
  1. allyl bromide
  2. vinyl chloride

Vinyls are monosubstituted ethylenes.
Allyls are propylenes attached to a backbone at the C3 position

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9
Q

What gets numbering priority, alkane substituents or halogen?

A

Halogens.

Example: 1-chloro-2-methylcyclohexane

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10
Q

What gets numbering priority, alcohols or alkenes?

A

Alcohols.

They have a higher oxidation state.

Example: hept-6-en-1-ol

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11
Q

How are ethers named?

A

With an alkoxy- prefix.

Ex: methoxyethane (C-O-C-C)

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12
Q

How are aldehydes named? What are some common name aldehydes?

A

Put an “-al” at the end to name aldehydes.

Two common names to know are:

  1. formaldehyde (methanal)
  2. acetaldehyde (ethanal)
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13
Q

What is acetone?

A

C
C=O
C

dimethyl ketone
2-propanone

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14
Q

What is the highest priority functional group?

A

Carboxylic acids.

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15
Q

What are the two primary considerations for comparing boiling points?

A
  1. Intermolecular forces (H bonding)

2. Molecular weight

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16
Q

In what solvent will Sn2 reactions happen most quickly?

A

Polar aprotic.

polar aprotic solvents create only weak intermolecular attraction between molecules; protic solvent can hydrogen bond

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17
Q

What is the difference in the D/L and S/R designations?

A

D/L, plane polarized light. L to the left. D to the right.

S/R, priority of atoms around a chiral carbon.

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18
Q

Anomer

A

An epimer at the anomeric carbon. Only possible in cyclic carbohydrate formation.

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19
Q

Epimer

A

When the H and OH of a carbohydrate has been changed in the Fisher projection.

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20
Q

Meso Compound (Meso Isomer)

A

Not optically active. Contains two chiral centers which are the mirror image of each other, so they cancel out.

     H
      I
Cl-C-OH
      I
Cl-C-OH
      I
     H
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21
Q

D-Mannose vs. L-Mannose

A

D: hydroxyl group furthest from C1 is on the right in open structure.

L: hydroxyl group furthest from C1 is on the left in open structure.

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22
Q

What is a furanose?

A

Carbohydrate structure with a 5-membered ring.

23
Q

What is an aldose?

A

When C1 is an aldehyde in a carbohydrate.

24
What is the alpha and beta position of carbohydrates?
Alpha: C1 hydroxyl is pointing down. Beta: C1 hydroxyl is pointing up.
25
What is a reducing sugar?
A sugar with an aldehyde group or a sugar capable of making an aldehyde group in solution through isomerization.
26
What does Ac2O (acetic anhydride) do when added to glucose?
It turns all the hydroxyl groups into AcO groups.
27
Fructose vs. Glucose vs. Mannose
Mannose: C1- aldheyde C2- OH on left Glucose: C1- aldehyde C2- OH on right Fructose: C1- CH2OH C2- carbonyl
28
What is the Fisher projection of glucose?
``` HC=O H C OH HO C H H C OH H C OH H2C OH ```
29
What is a glycoside?
A sugar that is attached to a non carbohydrate moiety (species/functional group).
30
If reacted with UV light and isobutane, which will produce a tertiary carbon? A. Fluorine B. Bromine C. Chlorine D. Iodine
Bromine is selective for secondary and tertiary carbons. F and Cl prefer primary carbons I makes most stable halogen in ionic form.
31
What does "oxo" refer to nomenclature?
Carbonyl.
32
What happens when there are three or more carboxylic acids on a carbon chain?
They are no longer counted in the main carbon backbone, but are named using a carboxylic acid suffix. Ex: 1-hydroxypropane-1,2,3-tricarboxylic acid
33
How to go from Fisher projection to R/S stereochemistry?
The arms come out to hug you.
34
What is the difference between enantiomers and diastereomers?
Enantiomer: Non-superimposable mirror image. Diastereomer: Non-superimosable, non-mirror image.
35
What is a racemic mixture?
When both R and S enantiomers are present in equal amounts which cancels out the optical activity, or rotation of plane polarized light.
36
What are some peaks to know for IR spectroscopy?
-OH: broad peak above 2900 cm-1 =O: sharp peak around 1700cm-1
37
How do you deshield protons in HNMR? What direction will the peaks move?
Deshielding protons = adding electronegative atoms. (It's like the proton is surrounded by a shield of electrons, and adding e-negative atoms pulls the shield away) Deshielding moves the peaks to the left.
38
How many peaks will equivalent protons split into?
n + 1 | this is for protons that are 3 bonds away
39
What are the general locations of the following HNMR spectra: 1. Alkyls 2. Alkenes 3. Aldehydes 4. Carboxylic acids
1. Alkyls: 1-3ppm 2. Alkenes: 4-7ppm 3. Aldehydes: 9-10ppm 4. Carboxylic Acids: 10-12ppm
40
What is UV spectroscopy useful for?
Studying compounds with double bonds and conjugated systems (which may involve lone pair(s) from heteroatoms).
41
How does Mass Spec work?
You get charge to mass value (m/z). X-axis has mass. Remember that H=1, C=12 and O=16, and try to find the discern the fragments from weight on the x-axis.
42
What is the general extraction principle? Or, the simple mneumonic to remember what dissolves what?
Like dissolves like.
43
How can pH be used to our advantage for extractions?
Dissociated acids will dissolve in the aqueous layer more readily because they are more polar.
44
What is the filtrate?
It's the liquid after filtering out a solid (the residue).
45
For recrystallization, what are the important properties of the solvent?
1. Solvent dissolves solute only at high temperatures. 2. It helps if solvent has a very low freezing temperature, so that solute can crash out before solvent freezes. For the Test: often a solvent with medium polarity is what is desired.
46
Which type of molecules move fast in normal TLC?
The non-polar substrate moves further up the silica gel paper, and the polar substrate travels less. It is the opposite in reverse-phase chromatography. The solvent is usually a mix of polar and non-polar to help the polar/non-polar molecules separate.
47
How does is column chromatography compare to TLC?
Column: uses gravity to separate molecules, polarity of solvents can be changed, silica beads make the column. Silica have pores. Big molecules fast. Small molecules slow.
48
SDS page can be affected by pH how?
low pH, species are protonated and migrate toward anode. high pH, species are deprotonated and migrate toward cathode.
49
How do you break glycosidic bonds?
Hydrolysis.
50
What is the only optically inactive AA?
Glycine.
51
What is the Henderson-Hasselbach equation?
pH = pKa + log([conj. base]/[conj. acid])
52
What are the four possible characterisitics of AA side chains?
1. polar 2. non-polar 3. basic 4. acid
53
How long is a peptide? What are the three atoms involved in the backbone? What is lost in a peptide linkage?
3 atoms long. N-C-COOH H2O is lost in the peptide linkage.
54
What are the following? 1. Amide 2. Imide 3. Imine
1. Imide: N with 2 functional groups O=C-N-C=O 2. Amide: N attached to a carbonyl carbon N-C=O 3. Imine: N double-boned to a carbon R-N=C-R2

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