Organic Chemistry 14C Flashcards
What is the formal charge of a Carbon with 4 bonds?
0
What is the formal charge of a Carbon with 3 bonds and 1 lone pair?
-1
What is the formal charge of a Carbon with 3 bonds?
+1
What is the formal charge of an Oxygen with 2 bonds and 2 lone pairs?
0
What is the formal charge of an Oxygen with 1 bond and 3 lone pairs?
-1
What is the formal charge of an Oxygen with 3 bonds and 1 lone pair?
+1
What is the formal charge of a Nitrogen with 4 bonds?
+1
What is the formal charge of a Nitrogen with 3 bonds and 1 lone pair?
0
What is the formal charge of a Nitrogen with 2 bonds and 2 lone pairs?
-1
What is the approximate pKa of Alkanes?
50
What is the approximate pKa of Alkenes?
43
What is the approximate pKa of Hydrogens?
36
What is the approximate pKa of Amines?
35
What is the approximate pKa of Alkynes?
25
What is the approximate pKa of Esters?
25
What is the approximate pKa of Nitriles?
25
What is the approximate pKa of Ketones?
20-24
What is the approximate pKa of Aldehydes?
20-24
What is the approximate pKa of Alcohols?
17
What is the approximate pKa of Water?
16
What does the acronym RICHES stand for?
Resonance, Induction, Charge, Hybridization, Electronegativity, Size
Is the conjugate base a positive or negative ion?
Negative, anion
Are more electronegative atoms that are closer in proximity make the molecule more or less acidic?
More acidic.
If a charge is more positive, is it more or less acidic?
More acidic.
If a charge is more negative, is it more or less acidic?
Less acidic.
Do more electronegative atoms stabilize charge better or worse?
Better.
True or False: The least electronegative atom is the least stable.
True
True or False: The most electronegative atom is the most stable.
True
Do p orbitals or s orbitals stabilize a negative charge better?
S orbitals
Which hybrid orbital type stabilizes electrons better? sp, sp2, or sp3?
sp, p orbitals are farther from the nucleus (+) and cannot stabilize as well.
Are lower or higher pKa’s more stable?
Lower pKa’s
Are bigger or smaller atoms more acidic?
Bigger atoms are more acidic.
True or False: Alkanes are soluble in water.
False, alkanes are non polar.
True or False: Alcohols are soluble in water.
True, shorter alkyl chains are more soluble
If there is an OH (hydroxyl) group, there is a _______.
Alcohol
Do alkanes or alcohols have higher boiling points?
Alcohols due to hydrogen bonding.
True or false: Except for methanol, alcohols are slightly less acidic than water.
True
Do ethers or alcohols have higher boiling points?
Alcohols. Ethers lack hydrogen bonding.
List the functional group priority list when naming a molecule (IUPAC).
- Alcohol
- Amine
- Ether
- Halogen
What is the difference between a bicyclo fused rign and a bicyclo bridged ring?
A fused ring has no carbons in the central bonds between two rings. A bridged ring can have one or more.
What are the electronegativities of Oxygen and Chlorine? Which one is more electronegative?
O = 3.44
Cl = 3.16
O > Cl
What are the electronegativities of Carbon and Hydrogen? Which one is more electronegative?
C = 2.55
H = 2.20
C > H
True or False: More electronegative atoms better stabilize negative charge (anion)?
True. Trend is true as you go across the periodic table.
What is a thiol?
Thiol is an organosulfur compound that contains a carbon-bonded sulfhydryl group. Thiols are the sulfur analogue of alcohols.
True or False: thiols (R-SH) are a bigger molecule than alochol yet have weaker intermolecular forces.
True. Alcohol can hydrogen bond while thiol canno.
When a thiol is not the highest priority, what is the nomenclature?
“mercapto”
i.e. 2-mercaptoheptan-4-ol
True or False: Alcohols are more acidic than thiols.
False
pKa around 13 for thiols, and 16 for alcohols
Are thiols soluble?
Somewhat, but less than alochols.
Are thiols polar?
Yes
How many degrees of saturation does a double bond count for?
1
How many degrees of saturation does a ring count for?
1
How many degrees of saturation does triple bond count for?
2
In Alkenes, when do you use the Cis/Trans labels? Which is Cis and which is Trans?
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.
