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PCAT > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

(64 cards)

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1
Q

Elements of Unsaturation

A

(CnH2n+2) - X

1 db= 1 unsat 1 tb = 2 unsat 1 ring=1 unsat

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2
Q

Boilping point

A

BP increases with incrased carbons. polar groups (EN atoms) will incnrease BP the heavier the polar group the higher the BP hydrogen bonds increase BP the most

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3
Q

Nucleophile

A

Lewis base (electron donor with bond formation)

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4
Q

electrophile

A

lewis acid (electron acceptor)

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5
Q

Conjugate bases + Stability

A

Stronger an acid, the more stable it’s conjugate base. Stability due to: 1. HIgher EN of an atom in conjugate base (applies for atoms in same row) 2. larger size (size applies for atoms in same column) 3. resonance stabilization

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6
Q

Common naming method

A

1C: form- 2C: acet- 3C: propion- 4C: butyr-

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7
Q

What is dis

A

Glycine

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8
Q
A

Alanine

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9
Q
A

serine

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10
Q
A

aspartic acid

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11
Q
A

cysteine

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12
Q
A

Amine

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13
Q
A

imine

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14
Q
A

amide

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15
Q
A

thiol

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16
Q

homolytic bond cleavage

A

one electron of the bond being broken goes to each fragment of the molecule

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17
Q

heterolytic bond cleavage

A

both electrons of the bond end up on the same atom (forms anion and cation)

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18
Q

anti conformation

A

largest group is 180 degrees apart

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19
Q

gauche conformation

A

larger group is 60 degrees apart

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20
Q

chair conformation stability

A

substitued groups are more stable in equatorial position

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21
Q

number of possible isomers formula

A

2^n chiral centers

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22
Q

enantiomer

A

non superimposable mirror images

RR/SS + SS/RR

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23
Q

diasteriomers

A

superimposible

SS/RR + RS/SR

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24
Q

melting point and boiling point of hydrocarbons

A

branching decreases

increased weight increases

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25
Free Radical Halogenation
Initiation: X-X \>\>hv\>\> **X\* + X\*** Propagation R-H + X\* \>\>\> R\* + HX R\* + X--X \>\>\> R---X + X\* Termination: X\* + X\* = X--x R\* + R\* \>\>\>\> R-R R\* + X\* \>\> R--X Peroxides inhibit this rxn Racemized product
26
Nucleophilicity
Increases as - charge increases increases going down periodic table in a group: F

going left in the periodic table

opposite of electronegativity trend
27
Sn2 Reaction
Reactivity of Substrate: CH3\>\> 1 \>\> 2 \>\> 3 (steric hindrance stereochemistry: inversion reaction rate= k [nuc][electro] polar aprotic (no Hbonds) strong non bulky nucs
28
Sn1 Reaction
Reactivity of substrate: 3\>\>2\>\>1 stereochem: racemization reaction rate= k[electro] protic Hbonding solvens carbocation rearrangements take place nonbasic weak nucs
29
E1 Reactions
3\>\> 2\>\> 1 stereochem: most substituted double bond trans over cis reaction rate = k [haloalkene] solvent: protic Hbonders carbocation rearangement weak bases high temp
30
E2 Reactions
3 \>\> 2 \>\> 1 stereochemistry: small bases yield most substituted; bulk yields least substituted reaction rate= k[base][substrate] polar aprotic non hbonder solvents no rearrangements strong bases;
31
Addition of Hydeogen halide to Alkene
marvoinokov addition of halide alkene is nucleophile
32
Oxymercuration demercuration
markovinokov addition of OH
33
Hydrohalide addition to alkene in peroxides
anti markovinokov addition of BR
34
hydroboration oxidation
antimarkovinokov addition of OH \* 1.BH3 if this is the only step BH2 is added antimarkovinovoley 2. h2o2, -oh
35
Hydration of alkenes
markovinokov addition of OH
36
Halogenation of Alkenes
chlorine or bromine adds anti addition racimization
37
epioxide formation from alkenes
alkene + peroxyacid = epoxide + carboxylic acid
38
MCBPA epoxidation with acidic/basic hydrolysis
If H20 is added after you get a transdiol
39
Potassium Permangate alekene reaction(s)
if basic solution added: cis-diol if acidic solution added: cleavage into ketones/aldehydes
40
Hydrogenation (with Ni/Pd/ or Pt) of alkenes
syn- addition of H-H MUST USE CATALYST
41
hydrogenation of alkyne (H2 and catalyst)
complete halogenation
42
hydrogenation of alkyne with lindlar
syn addition
43
alkene + Na, NH3(l)
trans addition
44
Aromatic Substitution of benzene
halogenation: Ph-H + Cl2/ AlCl3 or Br2/FeBr3 \>\>\>\> Ph-Cl + HCl or Ph-Br + HBr Nitration: Ph-H + HNO3 + H2SO4\>\>\>\> Ph-NO2 + H20 Alkylation: PhH + RCl/AlCl3 \>\>\> Ph-R + HCl
45
Ring Activation groups
increase bonding to benzene; lone pair of electrons on atom directly bonded to ring (electron donation group) ortho para directors (halogens do this as well)
46
Ring deactivation groups
decrease bonding to benzene + charge or no electrons electron withdrawing meta directors
47
Reduction of aldehydes, carboxylic acids, ketones, and esters
carboxylic acids, esters, aldehyde: primary alcohol ketone: secondar alcohol
48
Gringard reagents and carbonyl groups
reduces carbonyl to OH and adds the R group
49
Forming alkyle halides from Alcohols
ROH+ SOCl2 \>\> RCL ROH+ PBR3 \>\> RBr ROH+ HCl \>\> RCl + H2O ROH + Cl2 \>\>\> No reacion hydroxide is a bad leaving group
50
PCC and primary alcohol
Changes OH to carbonyl; loses H+
51
secondary alcohol and pcc/kmno4
ketone
52
Wittig Reaction
changes ketone to Alekene bond
53
Imine Formation from ketone/aldehyde
Replaces O with N-R'
54
aldol condesation
basically doubles the molecule and one =O \>\> to -OH iif and heat is added the OH (dehydration) is removed and forms a double bond
55
Carboxylic acid acidity
stability of the carboxylate ion makes carboxylic acids more acidic than alcohols EWG increase acidity; EDG decrease acidity
56
Reduction of Carboxylic acids
yields primary alcohol
57
Carboxylic Acid to Acid chlorides
adding SOCL2, PCl3, PCl5
58
carboxylic acid to acid anhydride
R'COOH + RCOCL + Pyridine \>\>\> RC=OOC=OR' +PyridineCL
59
Carboxylic acid + alcohol
esterification; must be in acidic environment
60
Acid chloride + ammonia
forms amide basically replace Cl with NH2
61
Ester + amine
amide. can be substituated
62
Reactivity of Carboxylic Acid derivatives
63
Saponification
64
Esters to Alcohols
RO=COR' \>\>reducing agent\>\> RCOH + R'OH

PCAT (5 decks)

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