Organic Chemistry 14C

Question 1

What is the formal charge of a Carbon with 4 bonds?

Answer 1

0

Question 2

What is the formal charge of a Carbon with 3 bonds and 1 lone pair?

Answer 2

-1

Question 3

What is the formal charge of a Carbon with 3 bonds?

Answer 3

+1

Question 4

What is the formal charge of an Oxygen with 2 bonds and 2 lone pairs?

Answer 4

0

Question 5

What is the formal charge of an Oxygen with 1 bond and 3 lone pairs?

Answer 5

-1

Question 6

What is the formal charge of an Oxygen with 3 bonds and 1 lone pair?

Answer 6

+1

Question 7

What is the formal charge of a Nitrogen with 4 bonds?

Answer 7

+1

Question 8

What is the formal charge of a Nitrogen with 3 bonds and 1 lone pair?

Answer 8

0

Question 9

What is the formal charge of a Nitrogen with 2 bonds and 2 lone pairs?

Answer 9

-1

Question 10

What is the approximate pKa of Alkanes?

Answer 10

50

Question 11

What is the approximate pKa of Alkenes?

Answer 11

43

Question 12

What is the approximate pKa of Hydrogens?

Answer 12

36

Question 13

What is the approximate pKa of Amines?

Answer 13

35

Question 14

What is the approximate pKa of Alkynes?

Answer 14

25

Question 15

What is the approximate pKa of Esters?

Answer 15

25

Question 16

What is the approximate pKa of Nitriles?

Answer 16

25

Question 17

What is the approximate pKa of Ketones?

Answer 17

20-24

Question 18

What is the approximate pKa of Aldehydes?

Answer 18

20-24

Question 19

What is the approximate pKa of Alcohols?

Answer 19

17

Question 20

What is the approximate pKa of Water?

Answer 20

16

Question 21

What does the acronym RICHES stand for?

Answer 21

Resonance, Induction, Charge, Hybridization, Electronegativity, Size

Question 22

Is the conjugate base a positive or negative ion?

Answer 22

Negative, anion

Question 23

Are more electronegative atoms that are closer in proximity make the molecule more or less acidic?

Answer 23

More acidic.

Question 24

If a charge is more positive, is it more or less acidic?

Answer 24

More acidic.

Question 25

If a charge is more negative, is it more or less acidic?

Answer 25

Less acidic.

Question 26

Do more electronegative atoms stabilize charge better or worse?

Answer 26

Better.

Question 27

True or False: The least electronegative atom is the least stable.

Answer 27

True

Question 28

True or False: The most electronegative atom is the most stable.

Answer 28

True

Question 29

Do p orbitals or s orbitals stabilize a negative charge better?

Answer 29

S orbitals

Question 30

Which hybrid orbital type stabilizes electrons better? sp, sp2, or sp3?

Answer 30

sp, p orbitals are farther from the nucleus (+) and cannot stabilize as well.

Question 31

Are lower or higher pKa's more stable?

Answer 31

Lower pKa's

Question 32

Are bigger or smaller atoms more acidic?

Answer 32

Bigger atoms are more acidic.

Question 33

True or False: Alkanes are soluble in water.

Answer 33

False, alkanes are non polar.

Question 34

True or False: Alcohols are soluble in water.

Answer 34

True, shorter alkyl chains are more soluble

Question 35

If there is an OH (hydroxyl) group, there is a \_\_\_\_\_\_\_.

Answer 35

Alcohol

Question 36

Do alkanes or alcohols have higher boiling points?

Answer 36

Alcohols due to hydrogen bonding.

Question 37

True or false: Except for methanol, alcohols are slightly less acidic than water.

Answer 37

True

Question 38

Do ethers or alcohols have higher boiling points?

Answer 38

Alcohols. Ethers lack hydrogen bonding.

Question 39

List the functional group priority list when naming a molecule (IUPAC).

Answer 39

1. Alcohol 2. Amine 3. Ether 4. Halogen

Question 40

What is the difference between a bicyclo fused rign and a bicyclo bridged ring?

Answer 40

A fused ring has no carbons in the central bonds between two rings. A bridged ring can have one or more.

Question 41

What are the electronegativities of Oxygen and Chlorine? Which one is more electronegative?

Answer 41

O = 3.44 Cl = 3.16 O \> Cl

Question 42

What are the electronegativities of Carbon and Hydrogen? Which one is more electronegative?

Answer 42

C = 2.55 H = 2.20 C \> H

Question 43

True or False: More electronegative atoms better stabilize negative charge (anion)?

Answer 43

True. Trend is true as you go across the periodic table.

Question 44

What is a thiol?

Answer 44

Thiol is an organosulfur compound that contains a carbon-bonded sulfhydryl group. Thiols are the sulfur analogue of alcohols.

Question 45

True or False: thiols (R-SH) are a bigger molecule than alochol yet have weaker intermolecular forces.

Answer 45

True. Alcohol can hydrogen bond while thiol canno.

Question 46

When a thiol is not the highest priority, what is the nomenclature?

Answer 46

"mercapto" i.e. 2-mercaptoheptan-4-ol

Question 47

True or False: Alcohols are more acidic than thiols.

Answer 47

False pKa around 13 for thiols, and 16 for alcohols

Question 48

Are thiols soluble?

Answer 48

Somewhat, but less than alochols.

Question 49

Are thiols polar?

Answer 49

Yes

Question 50

How many degrees of saturation does a double bond count for?

Answer 50

1

Question 51

How many degrees of saturation does a ring count for?

Answer 51

1

Question 52

How many degrees of saturation does triple bond count for?

Answer 52

2

Question 53

In Alkenes, when do you use the Cis/Trans labels? Which is Cis and which is Trans?

Answer 53

When identical groups lie on either side of the double bond. Cis is when the groups are in the same direction. Trans is when the groups are oriented in opposite directions.