Organic Chemistry - Rules/Basics

studied byStudied by 34 people
5.0(2)
Get a hint
Hint

Draw: Neutral Fully Bonded Boron (2 ways)

1 / 81

flashcard set

Earn XP

82 Terms

1

Draw: Neutral Fully Bonded Boron (2 ways)

Key - 3 Bonds

<p>Key - 3 Bonds</p>
New cards
2

Draw: Neutral Fully Bonded Carbon (3 ways)

Key - 4 Bonds

<p>Key - 4 Bonds</p>
New cards
3

Draw: Neutral Fully Bonded Nitrogen (2 ways)

Key - 3 Bonds + 1 Lone Pair

<p>Key - 3 Bonds + 1 Lone Pair</p>
New cards
4

Draw: Neutral Fully Bonded Oxygen (2 ways)

Key - 2 Bonds + 2 Lone Pairs

<p>Key - 2 Bonds + 2 Lone Pairs</p>
New cards
5

Draw: Neutral Fully Bonded Fluorine (1 way)

Key - 1 Bond + 3 Lone Pairs

<p>Key - 1 Bond + 3 Lone Pairs</p>
New cards
6

Identify: The Charged Atom In This Molecule

Nitrogen - Has four bonds, no lone pair, results in + charge

<p>Nitrogen - Has four bonds, no lone pair, results in + charge</p>
New cards
7

Identify: The Charged Atoms In This Molecule

Rightmost Oxygen - 3 lone pairs, one bond, results in - charge 3rd Right Carbon - 3 bonds, results in + charge

<p>Rightmost Oxygen - 3 lone pairs, one bond, results in - charge 3rd Right Carbon - 3 bonds, results in + charge</p>
New cards
8

Which atom(s) have an oxidation state of -1 (bonded with Carbon)?

Hydrogen (H) and Boron (B)

New cards
9

Which atom(s) have an oxidation state of +1 (bonded with Carbon)?

Nitrogen (N), Oxygen (O), Sulfur (S), Halogens: Fluorine (F), Chlorine (Cl), Bromine (Br), Iodine (I)

New cards
10

Which atom(s) have an oxidation state of 0 (bonded with Carbon)?

Carbon

New cards
11

Assign oxidation states to each molecule:

Left to right: 0, +1, +2, +3, +4

<p>Left to right: 0, +1, +2, +3, +4</p>
New cards
12

True or False: Molecules Rapidly Switch Between Resonance Structures

False, in truth the molecule exits in between the resonance structures

New cards
13

True or False: Curly arrows showing the making/breaking of sigma bonds are found in both reaction and resonance diagrams

False, curly arrows that make or break sigma bonds are found ONLY in reaction diagrams

New cards
14

Draw: The Trend of Electronegativity on the Periodic Table

knowt flashcard image
New cards
15

Draw: The Trend of Atomic Radii on the Periodic Table

knowt flashcard image
New cards
16

Rank from Most to Least Electronegative: N, B, C, F

F,N,C,B

New cards
17

Rank from Largest to Smallest: F, C, B, O

B,C,O, F

New cards
18

Rank from Smallest to Largest Difference in Electronegativity: Ionic Bonds, Polar Covalent Bonds, Covalent Bonds

Covalent, Polar Covalent, Ionic

New cards
19

True or False: Bond Length is Directly Proportional to Bond Strength. Explain your answer.

False between different elements since ionic/covalent components come into play (most ionic = strongest). True between the same elements

New cards
20

Rank from Shortest to Longest: Single Bonds, Double Bonds, Triple Bonds (between the same elements)

Triple Bonds, Double Bonds, Single Bonds

New cards
21

True or False: Triple Bonds are Stronger than Single Bonds, explain.

True, triple bonds are shorter and therefore stronger than the longer, weaker, single bonds.

New cards
22

Describe: Ionic Interactions

Interactions between ions, full +/- charges on atoms

New cards
23

Describe: Hydrogen Bonding Interactions

Bonds between Hydrogen and a more electronegative atom (O,N,S,Cl,F)

New cards
24

Describe: Dipole Interactions

A single molecule experiences charge (polarity) without the presence of another molecule (affects the orientation of molecules near each other)

New cards
25

Describe: van der Waals Interactions

Interactions between two non-polar molecules resulting in an induced dipole (the dipole is not present in individual molecules)

New cards
26

True or False: Intermolecular Forces that are More Sensitive to Distance are Stronger

False, the more sensitive a force is to distance the weaker the force is. For example, the weakest intermolecular force (van der Waals) is very sensitive to distance.

New cards
27

Which Molecule Would Have a Higher Boiling Point, CH3CH2(OH)CH3 or C9H20

Despite the presence of hydrogen bonding, and a dipole in CH3CH2(OH)CH3, the abundance of weak van der Waals forces in C9H20 result in greater overall strength in the molecule, thus resulting in a higher boiling point.

New cards
28

Would CH3F or CH3I have a higher boiling point?

While CH3F contains the most electronegative molecule (strong dipole moment), Iodine has 53 electrons, each of which acts as a van der Waals force. Strength in numbers, CH3I has a much higher boiling point

New cards
29

True or False: The Structure (Physical Shape) of a Molecule has No Effect on Boiling Point

False, molecules that are flatter (easier to stack) have higher boiling points than molecules that are "rounder" in shape, even if the number and type of molecules are the same.

New cards
30

What important features do we need to consider when determining the best resonance structure? Rank them in descending order of importance.

  1. Full octets on all atoms (over is worse than under)

  2. Minimum amount of charge (total number of +/- charges)

  3. Charges match electronegativity

  4. Minimized distance between charges

New cards
31

What is a rule for determining the hybridization of an atom?

Number of bonding domains (bonds + lone pairs) minus 1.

New cards
32

Are sp, sp2, or sp3 bonds shorter, why?

sp. S orbitals are held closer to the nucleus of the atom, so hybrid orbitals with more s character make shorter bonds. (stronger bonds)

New cards
33

What do hybrid orbitals make, what do p orbitals make?

Hybrid orbitals make sigma bonds or hold lone pairs P orbitals make pi bonds or hold lone pairs

New cards
34

True or False: Every atom must have the same hybridization in every resonance structure

True

New cards
35

If the initial energy gap is large, how will orbital energy levels change upon mixing? What if the gap was small?

A large initial energy gap results in a small change in orbital energy levels A small initial energy gap results in a large change in orbital energy levels

<p>A large initial energy gap results in a small change in orbital energy levels A small initial energy gap results in a large change in orbital energy levels</p>
New cards
36

How does orbital overlap change orbital energy levels?

A greater overlap results in a large change in orbital energy levels Less overlap results in a small change in orbital energy levels

<p>A greater overlap results in a large change in orbital energy levels Less overlap results in a small change in orbital energy levels</p>
New cards
37

Define: Nucleophile

Nucleus loving, hence electron rich, electron donor, Lewis base

New cards
38

Define: Nucleophilicity

How nucleophilic a nucleophile is

New cards
39

Define: Electrophile

Electron loving, hence electron poor, electron acceptor, Lewis acid.

New cards
40

Define: Electrophilicity

How electrophilic and electrophile is

New cards
41

Draw an oxonium ion

A (+) oxygen with three bonds

<p>A (+) oxygen with three bonds</p>
New cards
42

What is a carbocation

A positively charged carbon with three bonds.

<p>A positively charged carbon with three bonds.</p>
New cards
43

What is the difference between an enol and an enolate?

Enol - OH bond Enolate - O(-)

<p>Enol - OH bond Enolate - O(-)</p>
New cards
44

What factors affect acidity?

Resonance Hybridization Electronegativity Polarizability Inductive effects Charge balance

New cards
45

How does electronegativity affect acidity?

More electronegative = more acidic

<p>More electronegative = more acidic</p>
New cards
46

How does hybridization affect acidity?

sp is most acidic, sp2 is intermediate, sp3 is least acidic From sp3 to sp2 pka changes by about 5, from sp2 to sp pka changes by about 20.

New cards
47

How do inductive effects affect acidity?

The presence of electronegative atom/atoms not attached to the H bond in question that influences the pka of the bond.

(The electronegativity of the atom/atoms, the number of atoms, and the proximity of the atom to the bond affect the strength of inductive effects)

Inductive effects make very minute changes

<p>The presence of electronegative atom/atoms not attached to the H bond in question that influences the pka of the bond.</p><p>(The electronegativity of the atom/atoms, the number of atoms, and the proximity of the atom to the bond affect the strength of inductive effects)</p><p><em>Inductive effects make very minute changes</em></p>
New cards
48

How does resonance affect acidity?

  1. "Share the burden" if the conjugate base of an acid is capable of sharing negative charges via resonance (more stable) the acid has a lower pka (more acidic)

  2. "Move charge to a new atom" if the charge can be moved to a new atom more suited to carry a charge the pka is reduced.

  3. "Hybridization" resonance structures determine hybridization

New cards
49

How does polarizability affect acidity?

Atoms with more electrons (lower in the periodic table) are easier to remove a proton from (more polarizable). More polarizable = lower pka.

New cards
50

Which side of an equilibrium equation is favoured?

The side of the equilibrium that is favoured is the one with a higher pKa

New cards
51

What are the rules for predicting bond strength?

  1. Bond order wins - lower bond order = stronger bons

  2. Atomic radius impacts bond length/strength (larger radii result in longer, weaker bonds)

  3. Lone pairs (in the second row) repel each other resulting in weaker bonds

New cards
52

How does hybridization affect C-H bond strength?

S orbitals are held closer to the nucleus of the atom, so hybrid orbitals with more s character make stronger bonds.

New cards
53

How does substitution affect C-H bond strength?

More surrounding bonds to carbon atoms result in weaker bond strength.

<p>More surrounding bonds to carbon atoms result in weaker bond strength.</p>
New cards
54

If a C radical is unstable, what do we know about the C-H bond it came from?

The C-H bond it came from was strong (it didn't want to break)

New cards
55

If a C radical is stable, what do we know about the C-H bond it came from?

The C-H bond it came from was weak (it was okay to break), there were more C-C bonds surrounding the C-H bond (substitution)

New cards
56

How does resonance affect bond strength?

Resonance involves delocalization of electrons over multiple bonds so they have both single and double bond character making them stronger than the single bond.

New cards
57

How do you determine the index of hydrogen deficiency?

(2x(# of carbon atoms) + 2) - (number of hydrogen atoms) or the number of rings + the number of pi bonds

New cards
58

Rank the stability of radicals that came from primary, secondary, and tertiary C-H bonds.

  1. Tertiary

  2. Secondary

  3. Primary

More surrounding C-C bonds make the C-H bond weaker and thus more stable as a radical

New cards
59

What are the three names for C-H bonds near C-C single bonds? What defines each?

Primary - 1 C-C bond surrounding the center C of the C-H bond Secondary - 2 C-C bonds surrounding the center C of the C-H bond Tertiary - 3 C-C bonds surrounding the center C of the C-H bond

<p>Primary - 1 C-C bond surrounding the center C of the C-H bond Secondary - 2 C-C bonds surrounding the center C of the C-H bond Tertiary - 3 C-C bonds surrounding the center C of the C-H bond</p>
New cards
60

What are the two names for C-H bonds near C-C double bonds? What defines each?

Vinylic (connected to a C=C bond) Allylic (beside a C=C bond)

<p>Vinylic (connected to a C=C bond) Allylic (beside a C=C bond)</p>
New cards
61

What are the two names for C-H bonds near C-C triple bonds? What defines each?

Acetylenic (connected to a C-C triple bond) Propargylic (next to a C-C triple bond)

<p>Acetylenic (connected to a C-C triple bond) Propargylic (next to a C-C triple bond)</p>
New cards
62

What are the two names for C-H bonds near benzene rings? What defines each?

Aryl (on the benzene ring( Benzylic (next to benzene ring)

New cards
63

What does a + Hf value indicate? What about a - Hf value?

A +Hf is less stable, a -Hf is more stable

New cards
64

How do branches affect stability?

More branches (number not length) create more stable molecules (in Alkanes)

New cards
65

Explain what each of these statements mean: Hf is more positive Hf is less negative Hc is more negative

ALL state the same thing: the molecule being described is less stable.

New cards
66

Are trans double bonds or cis double bonds more stable?

Trans bonds are more stable because they have fewer steric interactions (non-bonding regions in close proximity). Rings are the exception since you can't have a trans ring)

New cards
67

How is stability determined in Alkenes and Alkynes?

How substituted the pi bond is (more C around the bond makes a stronger bond)

New cards
68

What are the reactivity factors of Cl for primary, secondary, and tertiary bonds?

Primary - 1 Secondary - 3.9 Tertiary - 5.2

New cards
69

What are the reactivity factors of Br for primary, secondary, and tertiary bonds? (approx)

Primary - 1 Secondary - 80 Tertiary - 1600

New cards
70

What are the steps of chain reactions? What is the purpose of each?

  1. Initiation (any steps that increase the number of unpaired electrons)

  2. Propagation (sum together net reaction + # of radicals are conserved)

  3. Termination (steps that consume unpaired electrons)

New cards
71

When using peroxides, what steps of a chain reaction change?

Only initiation

New cards
72

How to C-C bonds connected to a benzene ring differ from other C-C bonds?

These C-C bonds are very weak, so the C-H bonds of the C next to a benzene ring are most likely to be broken and replaced with a halogen

New cards
73

Are sp2/sp bonds involved in radical halogenation?

No, these bonds are too strong to be involved in radical halogenation. Weaker bonds are of most interest

New cards
74

When are the # of types of C greater than the # of types of H?

When one or more C atoms have no H attached

<p>When one or more C atoms have no H attached</p>
New cards
75

When are the # of types of H greater than the # of types of C?

When there are protic functional groups (OH, NH, SH etc), or when the structure of the molecules is such that hydrogens can be identified from any direction

<p>When there are protic functional groups (OH, NH, SH etc), or when the structure of the molecules is such that hydrogens can be identified from any direction</p>
New cards
76

What does the range below 1500 represent on an IR spectrum?

Single bonds to carbon

New cards
77

Where are double bonds to Carbon found on the IR spectrum?

~1500-~1800

New cards
78

Which kind of bonds fall between 2000-2500 on an IR spectrum?

Triple bonds to Carbon

New cards
79

Where are bonds to hydrogen (OH, NH, CH) on an IR spectrum?

Above 2500

New cards
80

Draw an OH group on an IR spectrum

Key: Deep, wide curve

<p>Key: Deep, wide curve</p>
New cards
81

Draw a standard NH2 group on an IR spectrum

Key: Two close bumps (NOT ALWAYS NH2)

<p>Key: Two close bumps (NOT ALWAYS NH2)</p>
New cards
82

Draw a standard NH group on an IR spectrum

Key: One bump (NOT ALWAYS NH! Two NH2 bumps could be very close together!)

<p>Key: One bump (NOT ALWAYS NH! Two NH2 bumps could be very close together!)</p>
New cards

Explore top notes

note Note
studied byStudied by 3 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 170 people
Updated ... ago
5.0 Stars(3)
note Note
studied byStudied by 162 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 17 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 57 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 131 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 31 people
Updated ... ago
5.0 Stars(1)
note Note
studied byStudied by 12 people
Updated ... ago
4.0 Stars(1)

Explore top flashcards

flashcards Flashcard90 terms
studied byStudied by 49 people
Updated ... ago
5.0 Stars(2)
flashcards Flashcard44 terms
studied byStudied by 12 people
Updated ... ago
5.0 Stars(2)
flashcards Flashcard45 terms
studied byStudied by 5 people
Updated ... ago
5.0 Stars(1)
flashcards Flashcard40 terms
studied byStudied by 27 people
Updated ... ago
5.0 Stars(1)
flashcards Flashcard31 terms
studied byStudied by 1 person
Updated ... ago
5.0 Stars(1)
flashcards Flashcard23 terms
studied byStudied by 2 people
Updated ... ago
5.0 Stars(2)
flashcards Flashcard160 terms
studied byStudied by 24 people
Updated ... ago
5.0 Stars(2)
flashcards Flashcard50 terms
studied byStudied by 1206 people
Updated ... ago
4.4 Stars(8)