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Organic Chemistry I > Chapter 1: Bonding In Organic Compounds > Flashcards

Chapter 1: Bonding In Organic Compounds Flashcards

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1
Q

Organic Chemistry

A

of structure, properties and reactions of organic materials (matter that contains carbon atoms)

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2
Q

how are carbon atoms linked in organic compounds

A

one or more atoms of carbon are covalently linked to atoms of other elements

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3
Q

what are the most common atoms of other elements that carbon is linked to in organic compounds

A
  • hydrogen
  • oxygen
  • nitrogen
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4
Q

what are not organic compounds

A

carbides, carbonates and cyanides

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5
Q

in 1828, who discovered another way that urea can be produced

A

Freidrich Wohler discovered that urea can be produced from inorganic compounds

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6
Q

how is each orbital characterized

A

by a unique set of quantum numbers

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7
Q

principal quantum number (n)

A

a whole number that specifies the electron shell and it related to the energy of the orbital

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8
Q

angular momentum quantum number (s,p,d,f)

A

describes the shape of the orbital

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9
Q

spin quantum number

A

the spin of an electron, it will be +1/2 or -1/2

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10
Q

what is the angular momentum quantum number of carbon

A

1s^2,2s^2,2p^2

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11
Q

what is the probability of finding an electron in the s orbital

A

this is where the probability is high, 90-95%

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12
Q

shape of s orbitals?

A

spherically symmetric

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13
Q

shape of p orbitals?

A

like dumbells

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14
Q

for what n numbers are p orbitals possible and not possible

A

not possible for n=1, but are possible for n=2 and higher

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15
Q

when n is greater than one, how many p orbitals are there per n value

A

there are 3 p orbitals for every value of n

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16
Q

octet rule

A

maximum stability results when an atom is isoelectronic with a noble gas, aka has 8 electrons in its valence shell (same as noble gases)

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17
Q

what is it called when an electron pair is shared between 2 atoms

A

a covalent bond

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18
Q

when is the octet rule most useful

A

in cases involving covalent bonds to Carbon, nitrogen, oxygen and fluorine (CNOF)

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19
Q

what is another name for a double bond

A

a pi bond

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20
Q

what is electronegativity

A

a measure of the ability of an element to attract electrons towards itself when bonded to another element

an electronegative element attracts electrons

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21
Q

who made the electronegativity scale and what is it

A

Pauline made the scale and it goes from 0-4

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22
Q

what is the most electronegative element

A

fluorine (F) (4)

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23
Q

how does a polar covalent bond happen

A

it is when atoms share electrons in their bond still, but not equally

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24
Q

relationship between electronegativity and polarity of a bond

A

the greater the difference in electronegativity, the more polar the bond

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25
Q

what is a dipole moment a measure of

A

it is a measure of the polarity of a bond, so more polar bonds mean a higher dipole moment

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26
Q

give an example of dipole moment and polarity using fluorine

A

since fluorine is the most electronegative, it will have the most polarity in a bond, and will therefore have the highest dipole moment

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27
Q

what is formal charge

A

the charge calculated for an atom in a lewis structure

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28
Q

what is the net charge

A

the sum of the formal charges

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29
Q

what does the formal charge correspond to the difference of

A

the difference between the number of valence electrons an atom has in the neutral free atom and the valence electron count for a covalently bonded atom

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30
Q

formal charge is shown as…

A

a + or - on a diagram

31
Q

what is connectivity/constitution

A

the order in which the atoms of a molecule are connected

32
Q

why is the constitution important in terms of lewis structure

A

they are necesary to write a lewis structure

33
Q

what are isomers

A

different compounds that have the same molecular formula

34
Q

what are constitutional isomers

A

isomers that differ in the order in which atoms are connected

35
Q

what is another name for constitutional isomers

A

structural isomers

36
Q

what is a condensed formula

A

it is abbreviated from the lewis structure and lists the groups of atoms in order

ex)
CH3CH2NH2

37
Q

can 2 or more lewis structures be written for certain compounds or ions?

A

yes

38
Q

when are lewis structures called resonance structures?

A

when they have the same connectivity of atoms and the same number of electrons and the same net charge

39
Q

what is a resonance hybrid

A

when molecules exist as an average of the resonance structures

is just the average of the resonance structures

40
Q

what is the relationship between resonance and stability

A

the more resonance, the more stable, because it can’t move as much and there is more structure

41
Q

8 Rules for Resonance Structures

A
  1. the atom connectivity must be the same (atoms can’t just totally move)
  2. Each must have the same number of electrons and the same net charge
  3. Must have the same number of unpaired electrons (dots in lewis structure)
  4. Second row elements (ex. N) must not have more than 8 valence electrons (can’t have 10, for example)
  5. The structure with the most bonding electron pairs is the most important ( for its chemical properties) (so double bond over single bond)
  6. The structure with the lower amount of charged atoms is more important
  7. The negative charge should be on the most electronegative atom and the positive charge should be on the least electronegative atom
  8. Resonance structures show electron delocalization and this electron delocalization stabilizes molecules. Resonance stabilization is highest if the resonance structures are equally stable
42
Q

3 main reasons why resonance structures are so important

A
  1. resonance structures and resonance hybrids better represent delocalization of electrons between atoms
  2. resonance structures help understand reactivity
  3. molecules or ions in which the electrons are delocalized are unusually stable
43
Q

relationship between NG and stability

A

the higher the NG content, the less stable

44
Q

when rxns form unstable products…

A

the reaction takes longer

45
Q

what is the most stable arrangement of groups attached to a central atom

A

when there is maximum separation (so the degree angle) between electron pairs

46
Q

in molecules such as water, what determines the overall shape (for example, bent)

A

the nonbonding electron pairs

47
Q

is valence shell electron repulsions more or less for bonded electron pairs

A

bonded electron pairs have less repulsion than nonbonded electron pairs, because they are kinda stuck together

48
Q

linear arrangement special rule

A

4 electron double bonds and 6 electron triple bonds are considered one group of electrons in terms of spatial requirements and therefore are linear. an example of this is carbon dioxide

49
Q

what is a dipole moment of a molecule

A

the sum of the individual dipoles, which happen when there are polar bonds

50
Q

what happens if the dipoles cancel (arrows go in opposite directions)

A

the net dipole moment is zero (this is the only time that the dipole is zero)

51
Q

how are reactivity and properties of molecules determined

A

by their strength and polarity

STRUCTURE = FUNCTION

52
Q

what are curved arrows used for

A

to track the flow of electrons in chemical reactions

53
Q

how to the curved arrows work

A

the arrow begins where the electrons were originally and points to where they end up

54
Q

what do X’s mean

A

halogens

55
Q

multiple curves arrows

A

can show how a reaction progresses, for example they can show a proton transfer reaction. can also show the movement of bonding electron pairs

56
Q

IN THE PRESENCE OF ACID

A

H2O CAN BE PROTONATED

57
Q

a bronsted acid is a

A

proton donor

58
Q

a bronsted base is a

A

proton acceptor

59
Q

in an acid base reaction, a proton is transferred from the…

A

acid to the base

proton donor => proton acceptor

60
Q

what are the acids and bases converted to in an acid-base reaction

A

a conjugate acid and conjugate base

61
Q

strong acids have _______ Ka’s and _______ pKa’s

A

high, low

62
Q

the stronger the acid, the ____________ its conjugate base

A

weaker

63
Q

what are the major factors that affect the acidity (3)

A
  • strength of the bond to hydrogen
  • electronegativity of the atoms from which the proton is lost
  • electron delocalization in the conjugate base
64
Q

what happens to the bond to the hydrogen as the halogen size increases

A

the bond to the hydrogen becomes weaker

charge on the conjugate base is more spread out with the larger halide anions

65
Q

why does electronegativity increase across the periodic table

A

the increased polarity of the bond to hydrogen increases the partial charge on the hydrogen which increases the electronegativity

66
Q

what is the relationship between electronegativity and acidity

A

electronegative elements can influence acidity by the inductive effect. The electron withdrawing effect increases the partial positive charge and stabilizes the conjugate base

67
Q

what happens to the acid when the conjugate base is stabilized by electron delocalization

A

the acid is stronger

68
Q

what type of acid and base does equilibrium favor in an acid-base reaction

A

equilibrium favors the weaker acid and weaker base

69
Q

how do you calculate the equilibrium constant

A

Ka of reactant acid/Ka of product acid

70
Q

how can you predict the direction of proton transfer

A

use the pKa’s

for example, the wekaer acid has a higher pKa, and so the higher pKa is favored at equilibrium

71
Q

Lewis acid

A

electron pair acceptor

72
Q

lewis base

A

electron pair donor

73
Q

lewis acid-base reaction

A

a non bonding electron pair on the base bonds to the acid. the acid and base may or may not have a formal charge

74
Q

what is the lewis acid base idea also relevant to

A

substitution reactions and bronsted lowry proton transfer reactions

Organic Chemistry I (9 decks)

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