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PCAT > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

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
Q

Free Radical Halogenation

A

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

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26
Q

Nucleophilicity

A

Increases as - charge increases

increases going down periodic table in a group: F<cl></cl>

<p>
going left in the periodic table</p>

<p>
opposite of electronegativity trend</p>

</cl>

27
Q

Sn2 Reaction

A

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
Q

Sn1 Reaction

A

Reactivity of substrate: 3>>2>>1

stereochem: racemization

reaction rate= k[electro]

protic Hbonding solvens

carbocation rearrangements take place

nonbasic weak nucs

29
Q

E1 Reactions

A

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
Q

E2 Reactions

A

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
Q

Addition of Hydeogen halide to Alkene

A

marvoinokov addition of halide

alkene is nucleophile

32
Q

Oxymercuration demercuration

A

markovinokov addition of OH

33
Q

Hydrohalide addition to alkene in peroxides

A

anti markovinokov addition of BR

34
Q

hydroboration oxidation

A

antimarkovinokov addition of OH

* 1.BH3 if this is the only step BH2 is added antimarkovinovoley

  1. h2o2, -oh
35
Q

Hydration of alkenes

A

markovinokov addition of OH

36
Q

Halogenation of Alkenes

A

chlorine or bromine

adds anti addition

racimization

37
Q

epioxide formation from alkenes

A

alkene + peroxyacid = epoxide + carboxylic acid

38
Q

MCBPA epoxidation with acidic/basic hydrolysis

A

If H20 is added after you get a transdiol

39
Q

Potassium Permangate alekene reaction(s)

A

if basic solution added: cis-diol

if acidic solution added: cleavage into ketones/aldehydes

40
Q

Hydrogenation (with Ni/Pd/ or Pt) of alkenes

A

syn- addition of H-H MUST USE CATALYST

41
Q

hydrogenation of alkyne (H2 and catalyst)

A

complete halogenation

42
Q

hydrogenation of alkyne with lindlar

A

syn addition

43
Q

alkene + Na, NH3(l)

A

trans addition

44
Q

Aromatic Substitution of benzene

A

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
Q

Ring Activation groups

A

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
Q

Ring deactivation groups

A

decrease bonding to benzene

+ charge or no electrons

electron withdrawing

meta directors

47
Q

Reduction of aldehydes, carboxylic acids, ketones, and esters

A

carboxylic acids, esters, aldehyde: primary alcohol

ketone: secondar alcohol

48
Q

Gringard reagents and carbonyl groups

A

reduces carbonyl to OH and adds the R group

49
Q

Forming alkyle halides from Alcohols

A

ROH+ SOCl2 >> RCL

ROH+ PBR3 >> RBr

ROH+ HCl >> RCl + H2O

ROH + Cl2 >>> No reacion

hydroxide is a bad leaving group

50
Q

PCC and primary alcohol

A

Changes OH to carbonyl; loses H+

51
Q

secondary alcohol and pcc/kmno4

A

ketone

52
Q

Wittig Reaction

A

changes ketone to Alekene bond

53
Q

Imine Formation from ketone/aldehyde

A

Replaces O with N-R’

54
Q

aldol condesation

A

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
Q

Carboxylic acid acidity

A

stability of the carboxylate ion makes carboxylic acids more acidic than alcohols

EWG increase acidity; EDG decrease acidity

56
Q

Reduction of Carboxylic acids

A

yields primary alcohol

57
Q

Carboxylic Acid to Acid chlorides

A

adding SOCL2, PCl3, PCl5

58
Q

carboxylic acid to acid anhydride

A

R’COOH + RCOCL + Pyridine >>> RC=OOC=OR’ +PyridineCL

59
Q

Carboxylic acid + alcohol

A

esterification; must be in acidic environment

60
Q

Acid chloride + ammonia

A

forms amide basically replace Cl with NH2

61
Q

Ester + amine

A

amide.

can be substituated

62
Q

Reactivity of Carboxylic Acid derivatives

A
63
Q

Saponification

A
64
Q

Esters to Alcohols

A

RO=COR’ >>reducing agent>> RCOH + R’OH

PCAT (5 decks)

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