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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. Combustion reaction occurs through a radical process
vicinal
peroxycarboxylic acid
absolute configuration
C3H8 + 5O2 = 3CO2 + 4H2O + heat
2. How many stereoisomers can a molecule have with n chiral centers
2^n
protic solvent
angle strain
sp
3. When boat flips
ring flip
vicinal
combustion - disproportionation - free - radical substitution - pyrolysis
2^n
4. 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
specific rotation
angle strain
allyl
mcpba
5. A sigma bond and two pi bonds
halogen
triple bond
electrophilic addition of X2
electrophilic addition of H2O
6. Nucleus lover. electron rich species that are attracked to charged atoms
nucleophile
structural isomers
chiral center
covalent bond
7. Two hydroxyl groups
mcpba
primary carbon
diol
saturated hydrocarbon
8. Diols with hydroxyl group on adjacent carbon
electrophilic addition of free radicals
vicinal
pyrolysis
anti conformation
9. If a compound is able to rotate plane polarized light.
chiral center
pyrolysis
racemic mixture
optical activity
10. Ozonolysis under hot acidic kmO4 - e.g. H2O2 condition
sp3
halogen
propionaldehyde
oxidizing
11. Arise from angle strain - torsional strian and nonbonded strain
structural isomers
ozonolysis
enantiomer
ring strain
12. When two atomic orbitals combine. obtained mathematically by adding or subtracting wave functions. if sings are the same - make bonding - if different - less stable antibonding.
C3H8 + 5O2 = 3CO2 + 4H2O + heat
molecular orbital
potassium permanganate
pi bond
13. Is bonded to only one other carbon atom
ethers
ozonolysis
primary carbon
enantiomer
14. Contain carbon carbon double bonds. Use same root of alkane but end with 'ene'
oxidizing
hot - acidic potassium permanganate
ring flip
Alkene
15. Results when nonadjacent atoms or groups compete for space. dominant source of energy in flagpole interactions of the boat conformation. thus it goes in various conformations like chair boat and twist.
electrophilic addition of HX
Alkyne
nonbonded strain
ionic bond
16. When two p orbitals line up in parallel and electron clouds overlap. it exsits over a single bond.
hybridization
pi bond
not ignored
ozonolysis
17. Electrons of pi bond are reactive and easily attacked by molecules that want e pair e.g. electrophiles.
stereoisomers
Vinyl
gauche conformation
electrophilic addition
18. 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
Alkane nomenclature
pi bond
catalytic hydrogenation
geometric isomers
19. Diol with hydroxyl group on same carbon
geminal
configuration
Alkyne
hot - acidic potassium permanganate
20. Water can be added to alkenes under acidic conditions. make carbocation. ends with alcohol
diol
electrophilic addition of H2O
acetaldehyde
not ignored
21. More likely it is to attract positively charged proton. nucleophilic strength decreses: RO->HO>RCO2>ROH>H2O
covalent bond
alcohol
enantiomer
basicity
22. In presence of peroxide - oxygen or ultraviolet light. antimarkonikov because they want a stable free radical. therefore X ends up on least subsituted carbon
molecular orbital
enantiomer
electrophilic addition of free radicals
Vinyl
23. A = observed rotation / concentration * length
specific rotation
markovnikov's rule
pyrolysis
primary carbon
24. Results when cyclic molecules must assume conformations that have eclipsed interactions
protic solvent
isomer
torsional strain
ring flip
25. What are the best leaving groups?
sp3
enantiomer
mcpba
weak bases
26. Two p orbital form pi and third p orbital combine with s to make two sp hybrid. 180 degree apart
oxidizing
sp
potassium permanganate
not ignored
27. What is produced when o3 with lialh4 or nabh4
electrophilic addition of free radicals
triple bond
combustion - disproportionation - free - radical substitution - pyrolysis
alcohol
28. Name for propanal
propionaldehyde
electrophile
catalytic hydrogenation
oxidation
29. Di - tri - t - sec - n -
Ignored
gauche conformation
achiral
electrophilic addition of X2
30. A molecule with an internal plane of symmetry
achiral
meso compound
primary carbon
Alkyne
31. Most similar. same molecule only at different points in their rotation. show them with newmans projections
enantiomer
angle strain
conformational isomer
electrophile
32. E of double bond act as lewis base and react with hydrogen of hx. make carbocation intermediate. use markonikovs rule
ethers
y- root - en -x-yne
sp2
electrophilic addition of HX
33. Compounds with halogen
electrophilic addition of free radicals
configuration
Haloalkane
saturated hydrocarbon
34. 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.
diastereomers
electrophilic addition of free radicals
chiral center
nonbonded strain
35. Nonterminal alkenes are cleaved to form two molar equivalent of carvoxylic acid ..make keton
electrophilic addition of HX
reducing
hot - acidic potassium permanganate
sp
36. Describes the exact spatial arrangement of groups of atoms independent of other molecules.
specific rotation
Alkene
enantiomer
absolute configuration
37. Creation of long - high molecular weight polymer composed of repeating subunit called monomers. occur through a radical mechanism.
electrophilic addition of X2
catalytic hydrogenation
diol
polymerization
38. Three different substitutents often have plane of symmetry. and rotation of 180 will allow molecule to be superimposed on mirror image
structural isomers
achiral
Alkyne
primary carbon
39. When bond angles deviate from ideal values
optical activity
enantiomer
angle strain
vicinal
40. Zn/h or CH3/s with ozonolysis
reducing
hybridization
triple bond
electrophile
41. Alkene oxidized with this - strong oxidizing agent. CH3CO3H or mcpba and it makes epoxide or oxirane
formaldehyde
y- root - en -x-yne
nucleophile
peroxycarboxylic acid
42. Name for mathanal
ozonolysis
covalent bond
formaldehyde
Alkyne
43. 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
gauche conformation
enantiomer
optical activity
pyrolysis
44. Carbon with four different substituents and lack a plane of symmetry
electrophilic addition of X2
gauche conformation
geminal
chiral center
45. Carbon carbon triple bonds. Suffix-yne.
racemic mixture
Alkyne
acetaldehyde
molecular orbital
46. Name for ethanal
allyl
acetaldehyde
catalytic hydrogenation
2^n
47. Always receive number one. contain carbonyl and OH group - very oxidized. highest priority functional group.
isomer
eclipsed conformation
sp2
carboxylic acid
48. Diborane add to double bond. boron acts as lewis acid and attaches to less hindered carbon. hydride transferred to adjacent carbon. antimarkonikov - alcohol produced
optical activity
hydroboration
pyrolysis
chiral center
49. Same chemical formula. same atomic connectivity . different in how atoms are arranged in space
stereoisomers
methylene
diol
initiation propagation termination
50. Refers to the =CH2 group
electrophilic addition of free radicals
meso compound
halogenation
methylene
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