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Organic Chemistry > Ch. 1 - Structure and Bonding > Flashcards

Ch. 1 - Structure and Bonding Flashcards

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1
Q

What is deuterium?

A

isotope of hydrogen (one proton, one neutron) (mass # = 2)

also relates to NMR spectroscopy!

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2
Q

Where are most elements in organic chemistry found within the periodic table?

A

1st and 2nd rows (s and p orbitals)

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3
Q

Which is higher in energy, s or p orbitals? Why?

A

p orbitals are higher in energy because the electron density is farther away (takes work to pull electron away, takes work to shield?)

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4
Q

What is electronegativity?

A

tendency to gain electrons

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5
Q

What is the formula for formal charge?

A

FC = val e- – (1/2 bonding + nonbonding e-)

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6
Q

What is an isomer?

A

same molecular formula, different structure + molecule

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7
Q

What atoms are common exceptions to octet rule? (BBPS)

A

boron and beryllium (2nd row; not enough e- in neutral molecule)
phosphorus, silver (3rd row; empty d orbitals, can have more than 8)

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8
Q

Where is hydrogen placed for all oxyacids? (ex. HNO3)

A

it is placed on oxygen

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9
Q

Where does organic chem assume hydrogens go?

A

on carbon

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10
Q

What does “resonance stabilized” mean?

A

molecule has 2 or more resonance structures; negative charge is spread over molecule aka electrons are delocalized

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11
Q

What is the formal charge of a single bonded oxygen with 3 lone pairs?

A

-1

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12
Q

What is the formal charge of a double bonded oxygen with two lone pairs?

A

0

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13
Q

What is curved arrow notation?

A

shows how electron position differs between structures

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14
Q

What is a heteroatom?

A

an atom other than carbon or hydrogen

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15
Q

What are the only things that vary for resonance strucutres?

A

lone pairs and pi bonds (and formal charge)

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16
Q

What is the most electronegative element?

A

fluorine

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17
Q

What is the 2nd most electronegative element?

A

oxygen

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18
Q

What are the 3rd most electronegative elements?

A

nitrogen and chlorine

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19
Q

What is a resonance hybrid?

A

composite of all possible resonance structures, electrons are delocalized

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20
Q

Why can carbon form four bonds where it should only have two open p orbitals?

A

It hybridizes to 4 sp3 hybrid orbitals

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21
Q

Which is stronger, a sigma bond or a pi bond?

A

a sigma bond is stronger because the electron density is closer to the nuclei (in between)

22
Q

What type of overlap occurs in sigma and pi bonds?

A 
sigma = end-end 
pi = side-side
23
Q

What is conjugation?

A
  • double/triple bonds that are separated by a single bond
  • occurs whenever p orbitals can overlap 3 adjacent atoms
  • conjugated systems have added stability
24
Q

What makes a better resonance structure?

A
  • more bonds and fewer formal charges
  • obeys octet rule
  • negative charge is on more electronegative atoms
  • positive charge is on less electronegative atoms
  • PRIORITIZE OCTET
25
Q

What is the difference between a shell and an orbital?

A 
Shell = principal quantum number/orbit
Orbital = actual electron density
26
Q

How many orbitals are in the first shell?

A

one

27
Q

Where is most of the volume of an atom contained?

A

electron cloud

28
Q

Does a chemical bond produce a system of higher or lower energy?

A

lower

29
Q

Atoms bond in order to achieve a full shell of _____ electrons, leading to a system that has _____ energy and increased stability, compared to the unbonded atoms.

A

valence; decreased

30
Q

T or F: A p orbital has the greatest electron density at the nucleus.

A

F, A p orbital has a node (region of zero electron density) at the nucleus.

31
Q

What is a constitutional isomer?

A

An isomer that has different connectivities (same molecular formula)

32
Q

T or F: Halogens are usually placed in the periphery of the molecule because they only form one bond.

A

False. That’s hydrogen.

33
Q

T of F: B and Be do not have sufficient electrons to have an octet.

A

True

34
Q

T or F: A resonance hybrid is a single structure.

A

True. It does not fluctuate between the resonance forms.

35
Q

What two things determine an atom’s geometry?

A

bond angle and bond length

36
Q

What is the basic principle of VSEPR theory?

A

groups around an atom are located as far from each other as possible

37
Q

T or F: The number of unpaired (single) electrons in a resonance structure cannot change.

A

True

38
Q

T or F: Lone pairs are omitted in condensed structures.

A

True (double check!)

39
Q

What two things does a charge on an atom indicate in a skeletal structure?

A

the number of covalent bonds and nonbonded electrons pairs at that atom

40
Q

What type of symmetry does a sigma bond have?

A

cylindrical symmetrical

41
Q

What is the ground state of an atom?

A

the lowest energy state of an atom where all electrons are in their lowest energy level

42
Q

When drawing a condensed structure of an organic compound, multiple bond lines are usually ______ while single bond lines are often ______.

A

Included, omitted

43
Q

For a carbon-carbon triple bond, what oritals overlap to form a sigma bond?

A

sp

44
Q

Unhybridized p orbitals are at what angle towards hybrid orbitals?

A

right angle

45
Q

T or F: Electronegativity is a relative quantity?

A

true

46
Q

What is the electronegative scale values?

A

0 to 4

47
Q

What is percent s character in sp, sp2 and sp3?

A

50%, 33%, 25%

48
Q

T or F: Any carbon-hydrogen bond is always considered to be polar.

A

False

49
Q

T or F: Pi bonds in a triple bond are perpendicular planes to each other.

A

true

50
Q

REMEMBER: Whenever C or H are bonded to O or N and halogens, they are polar!

A

Remember this!

Organic Chemistry (26 decks)

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