The basics
Stereochem
Reactions you need to remember
Mechanisms
New stuff
100
What type of carbocation (primary, secondary, tertiary, or allylic) is the most stable?
Tertiary
100
What is a carbon atom attached to four different groups called?
Chiral center
100
What are the reagents used in catalytic hydrogenation?
H2 and a metal catalyst (Pd/C, Pt/C, Ni/C)
100
What do curved arrows depict when drawing mechanisms?
Movement of e-
100
What functional group is composed of an oxygen atom bonded to two R groups?
Ether
200
How would the dipole moment of a carbonyl be drawn?
With the arrow starting at the carbon and pointing toward the oxygen
200
A _____ compound is achiral and has an internal plane of symmetry
Meso
200
NaBH4 and LiAlH4 are examples of _____ agents
Reducing
200
What are the three main steps of all radical reactions?
Initiation, propagation, termination
200
_____ _____ makes epoxides more reactive/subject to opening than normal ethers
Ring strain
300
What are the four main factors that influence the acidity of a molecule?
ARIO
Atom, resonance, induction, orbital
300
How many chiral centers does this molecule have?
2
300
What is the difference in the products of acid-catalyzed hydration (with H2SO4/H2O) and hydroboration oxidation (with BH3/THF and NaOH/H2O2)?
Acid-catalyzed yields the Markovnikov product
Hydroboration oxidation yields the anti-Markovnikov product
300
When a nucleophile attacks a carbonyl carbon, where do the pi electrons in the C=O bond go?
To the oxygen atom, forming an alkoxide intermediate
300
Compared with oxygen ethers, _____-containing compounds (such as thioesters) are more nucleophilic
Sulfur
400
What is the hybridization of the nitrogen atom?
sp2
400
In a cyclohexane chair conformation, what position do bulky substituents prefer?
Equatorial
400
What functional group results from a reaction between a primary alcohol and pyridinium chlorochromate (PCC)?
Aldehyde
400
A tertiary alkyl bromide reacts with NaOH in an aprotic solvent. Will this reaction proceed via an Sn1, Sn2, E1, or E2 mechanism?
E2
400
What two reagents react with an alcohol to yield an ether in a Williamson ether synthesis?
A strong base and R-X group (X = Br, I)
500
Which is the most stable conjugate base: OH-, NH2-, Cl-, or F-?
Cl-
500
Is the carbon atom bonded to the chlorine atom in the R or S configuration?
S
500
What product results from a reaction between an alkene and peroxy acid/peracid (RCO3H, MCBPA, etc.)?
Epoxide
500
Under strongly acidic conditions, what happens to a carbonyl's oxygen atom before a nucleophilic attack occurs?
The oxygen is protonated
500
In _____ conditions, the less-substituted carbon atom of an epoxide is attacked by a nucleophile to open the ring
Basic