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AU 24 FINALS > ORG 1 > Flashcards

ORG 1 Flashcards

1
Q

addition rxn

A

from pi bond to no pi bond

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2
Q

hydrohalogenation mechanism

A

carbocation

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3
Q

hydration mechanism

A

carbocation

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4
Q

markovnikov addition

A

x on more substituted carbon

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5
Q

anti-markovnikov addition

A

x on less substituted carbon

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6
Q

halogenation mechanism

A

anti

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7
Q

halohydrin mechanism

A

anti

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8
Q

oxymercuration-demercuration mechanism

A

anti

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9
Q

hydrogenation mechanism

A

syn

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10
Q

hydroboration-oxidation mechanism

A

syn

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11
Q

hydroboration-oxidation regiochemistry

A

anti-markovnikov (only one for alkenes)

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12
Q

dihydroxylation mechanism

A

syn

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13
Q

carbene cyclopropanation mechanism

A

syn

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14
Q

epoxidation w/ m-CPBA mechanism

A

syn

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15
Q

ozonolysis mechanism

A

oxidative cleavage

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16
Q

KMnO4 cleavage mechanism

A

oxidative cleavage

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17
Q

are alkenes and alkynes the nuc or the electrophile

A

nuc

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18
Q

lindlar catalyst

A

Pd-CaCO3, Pb(OAc)2, Quinoline

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19
Q

quinoline is considered…

A

poison

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20
Q

why does the dissolving-metal reduction create a trans alkene?

A

because it is a radical mechanism

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21
Q

H2 and lindlar cat. make what product?

A

cis alkene

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22
Q

hydrohalogenation of alkyne with 1 equiv of reagent makes…

A

alkene

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23
Q

hydrohalogenation of alkyne with xs reagent makes…

A

alkane

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24
Q

hydration of alkyne makes…

A

ketone (not matter the # of equiv)

25
Q

hydroboration of alkyne makes…

26
Q

internal alkyne w/ ozonolysis makes…

A

2 carboxylic acids

27
Q

terminal alkyne w/ ozonolysis makes…

A

1 carboxylic acid and CO2 gas

28
Q

are vinyl cations stable

29
Q

vinyl cation

A

carbocation on a double bond

30
Q

conjugation

A

orbital overlap allowing delocalization of e- density

31
Q

polyene

A

a molecule with 2 or more double/triple bonds

32
Q

cumulated (allenes) polyene

A

zero sigma bonds between pi bonds

33
Q

conjugated polyene

A

1 sigma bond between pi bonds

34
Q

isolated polyene

A

2 or more sigma bonds between pi bonds

35
Q

isolated dienes are have ———- energy than conjugated dienes

36
Q

conjugated dienes have ——— energy than alkenes

37
Q

conjugate addition products

A

-1,2 addition
-1,4 addition

38
Q

1,2 addition product type

A

kinetic (faster), exists in cold temps

39
Q

1,4 addition product type

A

thermodynamic ( more stable), exists at room temp and hot temps

40
Q

diels alder rxn nuc

A

conjugated diene

41
Q

diels alder rxn electrophile

A

alkene/alkyne (aka dieneophile)

42
Q

diels alder rxn has up to —– contiguous stereocenters

43
Q

EDG (electron donating groups)

A

-R groups (induction)
-LP e- next to it (resonance)

44
Q

EWG (electron withdrawing groups)

A

-halogens (induction)
-CF3 (induction)
-pi bond w/ EN atom (resonance)

45
Q

the bond strength of radicals are similar to…

A

carbocations

46
Q

what 3 factors stabilize a radical

A

hyperconjugation, induction, resonance

47
Q

radical reaction indicators

A

heat, light energy, peroxide or azo

48
Q

3 steps in a radical reaction

A

initiation, propagation, termination

49
Q

initiation step (general)

A

from zero radicals to 2 radicals

50
Q

propagation step (general)

A

from 1 radical to 1 different radical

51
Q

termination step (general)

A

2 radicals to zero radicals

52
Q

what elements follow an early TS (exo)

53
Q

what elements follow a late TS (endo)

54
Q

Iodine radical only reacts with …

A

tertiary C or resonance

55
Q

Br radical reacts with…

A

majority: tertiary C (usually)
very small minority: secondary and primary

56
Q

Cl radical reacts with…

A

secondary or tertiary C

57
Q

F radical reacts with…

A

tertiary, secondary, or primary C

58
Q

peroxide effect stereochemistry

A

racemization (like SN1)

59
Q

peroxide regioselectivity

A

anti-markovnikov

AU 24 FINALS (3 decks)

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