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MCAT Organic Chemistry
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Subjects
:
mcat
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science
Instructions:
Answer 50 questions in 15 minutes.
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Match each statement with the correct term.
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This is a study tool. The 3 wrong answers for each question are randomly chosen from answers to other questions. So, you might find at times the answers obvious, but you will see it re-enforces your understanding as you take the test each time.
1. Refers to the =CH2 group
chiral
combustion - disproportionation - free - radical substitution - pyrolysis
methylene
lindlar's catalyst
2. Two hydroxyl groups
configuration
molecular orbital
acetaldehyde
diol
3. Reducing an alkene by adding molecular hydrogen to double bond with aid of metal catalyst. e.g. pt - pd - ni. takes place on surface of metal so it does syn addition
catalytic hydrogenation
fischer projection
Alkane
anti conformation
4. Y = position of double bond - x is position of triple bond - root is the prefix representing the length of the principal carbon chain
y- root - en -x-yne
Combustion
ring strain
electrophile
5. Transfer of electrions from one atome to another
ionic bond
relative configuration
nucleophile
ketone
6. If reagent has a bunch of oxygen
oxidation
diol
acetaldehyde
anti conformation
7. If a compound is able to rotate plane polarized light.
cold potassium permanganate
reducing
C3H8 + 5O2 = 3CO2 + 4H2O + heat
optical activity
8. Alkene oxidized with this - strong oxidizing agent. CH3CO3H or mcpba and it makes epoxide or oxirane
vicinal
sigma bond
peroxycarboxylic acid
absolute configuration
9. Electrons of pi bond are reactive and easily attacked by molecules that want e pair e.g. electrophiles.
ethers
electrophilic addition
Vinyl
halogen
10. Monosubstituted ethylene
Vinyl
diastereomers
hot - acidic potassium permanganate
electrophilic addition of HX
11. Non mirror image of configurational isomers. cis and trans alkenes are them. possible when a molecule has two or more stereogenic centers that differ at some but not alll of the centers. they require multiple chiral centers.
aldehyde
eclipsed conformation
diastereomers
ketone
12. Zn/h or CH3/s with ozonolysis
reducing
structural isomers
ethers
electrophilic addition of free radicals
13. Carbonyl located at the end of the chain named by replacing al with e. e.g. butanal
hydroboration
protic solvent
electrophile
aldehyde
14. Not solvated
diastereomers
pi bond
aprotic solvent
isomer
15. A sigma bond and two pi bonds
aprotic solvent
Alkene
triple bond
eclipsed conformation
16. E of double bond act as lewis base and react with hydrogen of hx. make carbocation intermediate. use markonikovs rule
electrophilic addition of HX
oxidizing
structural isomers
carbonyl
17. Name for propanal
eclipsed conformation
propionaldehyde
sp
ring strain
18. Diborane add to double bond. boron acts as lewis acid and attaches to less hindered carbon. hydride transferred to adjacent carbon. antimarkonikov - alcohol produced
sp2
ring strain
hydroboration
Ignored
19. Highest energy no separation. or 120 separation.
formaldehyde
triple bond
Acetylene
eclipsed conformation
20. Moleculse that have the opposite configuration at their one chiral center. or if multiple chiral centers - must have the opposite configuration at every one of their chiral centers to be enantiomers. identical physical properties and much of the same
polymerization
enantiomer
fischer projection
allyl
21. Nitrogen containing compound - longest chain attached to nitrogen used in backbone. use e and replace with AMINE. if more complex molecule present - use prefix amino. IF additional group added - use N-
sigma bond
electrophilic addition of free radicals
ionic bond
amines
22. Iso - neo - cyclo
torsional strain
not ignored
propionaldehyde
ethers
23. What is produced when o3 with lialh4 or nabh4
alcohol
electrophilic addition
formaldehyde
eclipsed conformation
24. When bond angles deviate from ideal values
angle strain
electrophilic addition of X2
electrophilic addition
Alkane
25. Results when cyclic molecules must assume conformations that have eclipsed interactions
oxidizing
torsional strain
aprotic solvent
Alkane
26. Is bonded to only one other carbon atom
carbonyl
electrophilic addition of X2
primary carbon
eclipsed conformation
27. When two p orbitals line up in parallel and electron clouds overlap. it exsits over a single bond.
nonbonded strain
pi bond
quantum numbers
diastereomers
28. Charged - need electrons
electrophilic addition of X2
amines
potassium permanganate
electrophile
29. Solvents with protons in solution - e.g. water or alcohol. large atoms tend to be better nucleophiles in here because they can shed the solvating protons around them and are more polarizable
isomer
nonbonded strain
chiral
protic solvent
30. M - chloroperoxybenzoic acid
Alkyne
diol
primary carbon
mcpba
31. Most similar. same molecule only at different points in their rotation. show them with newmans projections
ozonolysis
peroxycarboxylic acid
Alkane
conformational isomer
32. Arise from angle strain - torsional strian and nonbonded strain
anti conformation
ring strain
alcohol
hot - acidic potassium permanganate
33. Cleaves double bond in half - it only oxidizes the carbon to an aldehyde under reducing conditions. if ozidizing make same product as KMNO4
ozonolysis
halogenation
potassium permanganate
ring strain
34. Diols with hydroxyl group on adjacent carbon
electrophilic addition of HX
nucleophile
covalent bond
vicinal
35. When boat flips
fischer projection
ionic bond
basicity
ring flip
36. Common name for ethyne
allyl
Acetylene
alkyne
C3H8 + 5O2 = 3CO2 + 4H2O + heat
37. Describes the exact spatial arrangement of groups of atoms independent of other molecules.
absolute configuration
electrophilic addition of H2O
halogenation
geometric isomers
38. Di - tri - t - sec - n -
acetaldehyde
Ignored
Combustion
ethers
39. Propylenes attached to a backbone at the C-3 position. Meaning the double bond at end of the chain and single bonded carbon at rest
combustion - disproportionation - free - radical substitution - pyrolysis
amines
allyl
formaldehyde
40. A molecule with an internal plane of symmetry
meso compound
halogenation
molecular orbital
angle strain
41. Combustion reaction occurs through a radical process
ionic bond
structural isomers
C3H8 + 5O2 = 3CO2 + 4H2O + heat
reducing
42. Ozonolysis under hot acidic kmO4 - e.g. H2O2 condition
pyrolysis
optical activity
oxidizing
carboxylic acid
43. Configuration in relation to another chiral molecule. use it to determine if a molecule is an enantiomer - diastereomer - etc
alkyne
relative configuration
pyrolysis
nucleophile
44. Carbon with four different substituents and lack a plane of symmetry
aldehyde
chiral center
torsional strain
y- root - en -x-yne
45. O3
2^n
potassium permanganate
electrophilic addition of H2O
ozonolysis
46. When a molecular orbital is formed head to head or tail to tail. all single bonds are tehese.
sigma bond
ionic bond
relative configuration
catalytic hydrogenation
47. Share molecular formula but have different chemical and physical properties
Alkyne
structural isomers
Alkene
ring flip
48. Two p orbital form pi and third p orbital combine with s to make two sp hybrid. 180 degree apart
halogenation
sp
molecular orbital
chiral center
49. A = observed rotation / concentration * length
specific rotation
covalent bond
diastereomers
sp3
50. Most favorable of staggared conformations
chiral
anti conformation
pyrolysis
eclipsed conformation
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