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Flashcards in Orgo Deck (44):
1

nucleophile

electron rich (lewis base)

2

electrophile

electron poor

3

heterocyclic compound

ring structure with atoms of more than one kind

4

achiral

symmetric molecule, no distortion of polarized light

5

amine

NH or NH2 group

6

amide

N directly attached to carbonyl carbon

7

carbonyl carbon

C=O

8

nitro group (electron donating or withdrawing? what type of director?)

NO2 attached, electron-withdrawing, meta-director

9

methyl and hydroxyl group (electron donating or withdrawing? what type of director?)

electron-donating, ortho- para director

10

How does # of electron withdrawing groups on phenol affect acidity?

More electron withdrawing groups attached= increased acidity

11

What stabilizes carbanions?

stabilized by electronegative groups or resonance with pi electrons (double bonds)

12

What is the order of free radical/ carbocation stability

tertiary > secondary > primary > methyl

13

vinylic cation

positive charge of intermediate is adjacent to a double bond, very unstable because pi bond is perpendicular to empty orbital and double bond can't delocalize the electrons

14

zwitterion

molecule with positive and negative charges, usually from compounds with acidic AND basic functional groups; strong intermolecular forces

15

Which resonance structure contributes most to actual structure?

the most energetically favorable resonance structure (no separation of charge = most stable)

16

How does chain length affect hydrogen bonding and boiling point?

decreases H-bonding strength, increases boiling point

17

How does branching affect boiling point?

decreases boiling point b/c decreases intermolecular strength

18

When does hydrogen bonding occur?

H is bound to N, O, F in compound

19

How does conjugation affect heat of hydrogenation?

increased conjugation = decreased heat of hydrogenation

20

acid anhydride

carboxylic acids linked with ester bond and loss of water

21

aromatic rings rxn mechanism

only follow electrophilic substitution reaction

22

SN1

carbocation, 2 steps, rearrangement is possible, affected by electronic factors, favored in polar protic solvents

23

SN2

no carbocation, 1 step/ 2nd order kinetics, affected by steric factors, inversion of configuration, needs nucleophile, favored in polar aprotic solvents

24

What is the order of best leaving groups in Halogens?

I > Br > Cl > F

25

racemic mixture

equal quantity of enantiomers

26

enantiomers

non-superimposable mirror images of chiral molecules; same physical and chemical properties; opposite configuration at every chiral carbon

27

diastereomers

not mirror image stereoisomers, same configuration at one or more chiral carbons

28

meso-compound

has internal plane of symmetry

29

geometric isomers

cis/ trans (Z/E)
different physical properties
describe position around double bond

30

Does cis or trans have higher boiling point?

cis has higher BP because of its permanent dipole moment

31

conformational isomers

rotation about a single bond (ie. boat/ chair and eclipse/gauche)

32

anomers

cyclic forms of carbohydrates that differ in configuration about Carbon 1

33

beta-oxidation

breakdown of body fat by breaking carbon chain of lipid into 2-carbon pieces to enter the TCA cycle

34

aromatic protons range on NMR

7-8ppm

35

esterification process

neucleophilic acyl substitution, Oxygen of alcohol attacks and adds to carbonyl carbon of carboxylic acid (R-C=O-OH) and water is lost to form ester

36

What type of reaction are double bonds susceptible to?

electrophilic addition

37

Markovnikov Rule

hydrogen adds to the least substituted carbon

38

Anti-markovnikov

occurs when alkene reacts with hydrogen halides in UV light or peroxide

39

Acetylating agents

introduce acetyl group (R-C=O-CH3)
acetyl chloride(CH3-C=O-Cl)
acetic anhydride (CH3-C=O-O-O=C-CH3)

40

grignard reagent

reacts with alcohol and carbonyl groups, but not ethers

41

allylic cation

cation with positive charge on the carbon adjacent to the carbon of the double bond (CH2=CH-C+)

42

acetone

aprotic and polar
promotes SN2 and E2
CH3-C(=O)-CH3 [keto form]
CH3-C(-OH)=CH2 [enol form]

43

ester

R-C(=O)-O-R

44

Heat of Hydrogenation

amount of energy released when pi bonds are converted to sigma bonds by addition of hydrogen

increased heat of hydrogenation= increased PE= decreased stability