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CHEM/OCHEM (MCAT) > Intro to Organic Chem > Flashcards

Intro to Organic Chem Flashcards

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1
Q

What does bond order describe?

A

whether a covalent bond is single, double or triple

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2
Q

What is the bond order of a single, double, and triple bond?

A

single –> bond order = 1
double –> bond order = 2
triple –> bond order = 3

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3
Q

How many sigma bonds and/or pi bonds are found in a single bond?

A

1 sigma bond

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4
Q

How many sigma bonds and/or pi bonds are founc in a double bond?

A

one sigma and one pi

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5
Q

How many sigma bonds and/or pi bonds are found in a triple bond?

A

one sigma bond and 2 pi bonds

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6
Q

TRUE or FALSE: potential energy is directly proportional to bond strength.

A

FALSE –> potential energy is inversely proportional to bond strength

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7
Q

TRUE or FALSE: bond length is inversely proportional to bond strenght.

A

TRUE

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8
Q

What is the formula for formal charge?

A

formal charge = (# of valence electrons in free atom) - (# of electrons in lone pair) - (# of bonds)

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9
Q

TRUE or FALSE: In a Lewis diagram, the central atom is usually the least electronegative.

A

TRUE

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10
Q

What are 4 things to look out for when determining the MAJOR resonance structure?

A
  1. full octet
  2. minimum number of formal charges
  3. negative FC on electronegative atoms
  4. minimum separation between opposite FCs
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11
Q

What does VSEPR stand for?

A

valence shell electron pair repulsion

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12
Q

TRUE or FALSE: lone pairs contribute to the determination of the geometry of a molecule, using VSEPR theory.

A

TRUE

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13
Q

Provide the number of groups, bond angle(s), central atom hybridization for the following basic geometry:

Linear

(note: number of groups = number of atoms and lone pairs connected to the central atom)

A

number of groups = 2
bond angle = 180
hybridization = sp

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14
Q

Provide the number of groups, bond angle(s), central atom hybridization for the following basic geometry:

Trigonal planar

(note: number of groups = number of atoms and lone pairs connected to the central atom)

A

number of groups = 3
bond angle = 120
hybridization = sp2

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15
Q

Provide the number of groups, bond angle(s), central atom hybridization for the following basic geometry:

Tetrahedral

(note: number of groups = number of atoms and lone pairs connected to the central atom)

A

number of groups = 4
bond angle = 109.5
hybridization = sp3

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16
Q

Provide the number of groups, bond angle(s), central atom hybridization for the following basic geometry:

trigonal bipyramidal

(note: number of groups = number of atoms and lone pairs connected to the central atom)

A

number of groups = 5
bond angle = 90, 120
hybridization = sp3d

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17
Q

Provide the number of groups, bond angle(s), central atom hybridization for the following basic geometry:

octahedral

(note: number of groups = number of atoms and lone pairs connected to the central atom)

A

number of groups = 6
bond angle = 90
hybridization = sp3d2

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18
Q

TRUE or FALSE: each bond in a double bond contributes individually to the hybridization of an atom.

A

FALSE –> double bonds do NOT contribute individually to hybridization

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19
Q

If an atom has a choice between sp2 and sp3, it chooses _______.

A

sp2

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20
Q

What is the geometrical name for a molecule that has 2 groups and alone pair?

A

bent

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21
Q

What is the geometrical name for a molecule with 2 lone pairs and 2 groups?

A

bent

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22
Q

TRUE or FALSE: electron delocalization decreases a molecule’s stability.

A

FALSE: electron delocalization INCREASES a molecule’s stability

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23
Q

What is the name of the rule used to determine if a compound is aromatic? Provide the guidelines.

A

Huckel’s Rule…a molecule is aromatic if it is:

  1. planar
  2. cyclic
  3. fully conjugated (alternating single and double bonds)
  4. contains a total of 4n+2 pi electrons (where n = 0, 1, 2, 3, etc.)

note: all carbons must be sp2 hybridized

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24
Q

TRUE or FALSE: if an atom has both a lone pair and a double bond, the lone pair does not contribute to aromaticity.

A

TRUE –> note that the double bond contributes to aromaticity

25
Q

TRUE or FALSE: if an atom has 2 lone pairs, both lone pairs contribute to aromaticity.

A

FALSE –> only one lone pair will contribute to aromaticity

26
Q

Define chiral.

A

any object that CANNOT be superimposed on its mirror image

27
Q

what are the 2 structural features of a stereogenic centre (chiral carbon)?

A
  1. the carbon will be sp3 hybridized (tetrahedral)

2. the carbon will be bound to 4 DIFFERENT atoms or groups

28
Q

In a fisher projection, what is the difference between the vertical and horizontal lines?

A 
vertical = going into the page
horizontal = coming out of the page
29
Q

What is a constitutional isomer?

A

structural isomers (different atom connectivity)

30
Q

What is a stereoisomer?

A

isomer with same atomic connectivity, but different arrangement in space

31
Q

What is a conformer/conformational isomer?

A

isomer with single bond rotation

32
Q

Arrange the following from least stable to most stable conformer:

gauche
anti
eclipsed

A

eclipsed < gauche < anti

33
Q

What letter of the alphabet designates a cis-alkene?

A

Z

34
Q

What letter of the alphabet designates a trans-alkene?

A

E

35
Q

If there are 3 substituents in an alkene isomer, how do you designate whether it is cis or trans?

A

Look for the higher priority group on each side of the double bond

36
Q

What is an enantiomer?

A

mirror image that cannot be superimposed

i.e. same connectivity but opposite configuration at EVERY chiral centre

37
Q

What are the 4 properties of enantiomers to keep in mind for the MCAT?

A

enantiomers:

  1. have opposite stereochemistry at ALL stereocenters
  2. have identical physical properties (bp, solubility, polarity)
  3. react identically in most environments
  4. react differently in a chiral environment
38
Q

How must the lowest priority atom/group be arranged on a molecule, when designating R and S configuration of a chiral centre?

A

the lowest priority atom/group must be pointing into the page

39
Q

Since enantiomers share identical physical properties, how can we tell them apart?

A

rotation of plane-polarized light

40
Q

Define dextrorotary. Is it designated with (+) or (-)?

A

(+)

rotate plane-polarized light to the right (clockwise)

41
Q

Define levorotatory. Is it designated with (+) or (-)?

A

(-)

rotate plane-polarized light to the left (counter-clockwise)

42
Q

What is a racemic mixture?

A

a 50:50 mixture of 2 enantiomers

43
Q

TRUE or FALSE: racemic mixtures result in a net rotation of plane-polarized light.

A

FALSE –> the 50:50 cancels out the rotation direction, so there is NO NET rotation

44
Q

What is one method of separating racemic mixtures?

A

React the enantiomers with another chiral molecule to produce diastereomeric salts.

45
Q

What are diastereomers?

A

stereoisomers that are not mirror images

must have at least one different stereocenter and at least one same stereocenter

46
Q

How do you calculate the maximum number of stereoisomers that a given molecule can have?

A

2^n

n = # of chiral centers

47
Q

What is a meso compound?

A

compound that contains a minimum of 2 chiral centers but is itself ACHIRAL

48
Q

TRUE or FALSE: meso compounds rotate plane-polarized light

A

FALSE –> meso compounds do not rotate plane-polarized light

49
Q

What are the 3 questions you should ask yourself when checking for meso compounds?

A
  1. Is there a minimum of 2 stereocentres?
  2. Is there a plane of symmetry?
  3. Are both halves of the molecule mirror images of each other (cannot be superimposed)?
50
Q

Thin layer chromatography, paper chromatography, and column chromatography separate mixtures based on:

a) size
b) specific affinity
c) boiling point
d) polarity
e) charge

A

d) polarity

51
Q

Gas chromatography separate mixtures based on:

a) size
b) specific affinity
c) boiling point
d) polarity
e) charge

A

c) boiling point

52
Q

Size-exclusion separate mixtures based on:

a) size
b) specific affinity
c) boiling point
d) polarity
e) charge

A

a) size

53
Q

Ion-exchange chromatography separate mixtures based on:

a) size
b) specific affinity
c) boiling point
d) polarity
e) charge

A

e) charge

54
Q

Affinity chromatography, paper chromatography, and column chromatography separate mixtures based on:

a) size
b) specific affinity
c) boiling point
d) polarity
e) charge

A

b) specific affinity

55
Q

What is the difference between stereospecific and stereoselective reactions?

A

stereospecific –> only create one kind of enantiomer

stereoselective –> favour one type of enantiomer, but still have some of amount of the other

56
Q

What is the name of the extraction technique used to separate a mixture of enantiomers by producing diastereomeric salts?

A

resolution

57
Q

In a liquid-liquid extraction, which layer is found on the top and which layer is found on the bottom? Describe the contents of the layers.

A

top = organic = large/less polar molecules

bottom = aqueous = small/more polar molecules, strong acids and bases, salts

58
Q

b

A

CHEM/OCHEM (MCAT) (10 decks)

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