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O Chem II CSCC > Addition Rxns > Flashcards

Addition Rxns Flashcards

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1
Q

in addition rxns, what 2 conditions require you to care about regiochemistry (deciding which nucleophile gets added to which carbon)?

A
  1. when you’re adding 2 different things (like a H and a Br)

2. when the receiving molecule is asymmetrical

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2
Q

in addition rxns, what is Markonikov addition?

A

what you call it when the non-hydrogen part of a nucleophile goes to the most substituted carbon on the electrophile.

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3
Q

are ‘anti’ addition and ‘anti-markonikov addition the same thing?

A

no

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4
Q

what is the difference between ‘anti’ addition and ‘anti-markonikov addition’?

A

anti addition means the two parts of the nucleophile are added to the electrophile on different planes.

anti-markonikov addition means the hydrogen in the nucleophile is added to the electrophile’s most substituted carbon

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5
Q

what does regiochemistry describe?

A

nucleophile behavior r/t how substituted the electrophile’s various carbons are

i.e, Markonikov addition

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6
Q

what does stereochemistry describe?

A

where the nucleophile components are in space

i.e. anti addition

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7
Q

what is the difference between ‘anti’ addition and ‘syn’ addition’?

A

anti addition adds nucleophile components to an electrophile on DIFFERENT planes

syn addition adds nucleophile components onto an electrophile on the SAME plane

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8
Q

which 3 metals can be used as catalysts for the hydrogenation addition rxn?

A

Pd, Pt, or Ni

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9
Q

what happens in an addition rxn?

A

2 groups get added ‘across’ a double bond

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10
Q

why does hydrogenation addition only do syn addition?

A

because both of the hydrogens have to be on the same side of the metal catalyst surface in order for the rxn to take place

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11
Q

which addition rxns make us have to care about meso compounds?

A

hydrogenation

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12
Q

do we have to care about regiochemistry (substituted-ness) in addition rxns that add 2 of the same thing to the receiving electrophile?

A

no

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13
Q

when do you have to care about syn and anti in addition rxns?

A

When you product has chirality on the carbons that the nucleophile(s) attacked

This gives you 2 products: the original and its enantiomer

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14
Q

what happens in a hydrohalogenation (HX) addition rxn?

A

the electrophile’s double bond attacks the nucleophile’s H. Then the nucleophile’s X attacks the electrophile’s most substituted carbon

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15
Q

does hydrohalogenation (HX) addition rxn make syn products or anti products?

A

both

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16
Q

does hydrohalogenation (HX) addition rxn make Markonikov products?

A

yes

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17
Q

why does hydrohalogenation (HX) addition rxn make both syn products and anti products?

A

bc it occurs in multiple steps including a carbocation formation

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18
Q

which addition reactions have carbocation intermediates/can do rearrangement?

A

hydrohalogenation (HX and HBr)

acid catalyzed hydration (H30+)

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19
Q

which addition rxn does anti-Markonikov addition with ROOR?

A

hydrohalogenation (HBr)

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20
Q

which addition rxn does anti-Markonikov addition even though it doesn’t use peroxides (like ROOR)?

A

hydroBORation oxidation (BH3)

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21
Q

which halogen works best for anti-markonikov addition?

A

Br. The other halogens don’t work for this.

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22
Q

does hydrohalogenation rxns with anti-markonikov addition (HBr) make syn products or anti products?

A

Both. HBr rxn makes a carbocation intermediate

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23
Q

does (acid-catalyzed) hydration do Markonikov addition?

A

yes

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24
Q

does (acid-catalyzed) hydration do anti addition or syn addition?

A

both. it makes a carbocation intermediate

25
Q

does hydroBORation do Markonikov addition or andi-markonikov addition?

A

anti.

It’s like hydration (in that it adds water across double bond), but it does anit mark

26
Q

which addition rxns add water across the double bond?

A

hydration (mark)
oximercuration-demercuration (mark)
hydroBORation (anti-mark)

27
Q

what happens in a hydroBORation (BH3) addition?

A

alkene becomes an alcohol:

double bond attacks H, then BH2 goes to LESS substituted carbon, then gets replaced by OH

28
Q

what are the reactants for hydroBORation (BH3) addition?

A

Step 1: BH3, THF

Step 2: H2O2, NaOH

29
Q

do hydroBORation (BH3) addition have carbocation intermediates/rearrangement?

A

no;

They make that weird square transition intermediate thing instead of carbocation intermediate.

30
Q

why do hydroBORation (BH3) addition rxn only do syn addition?

A

because they make that weird square transition intermediate thing instead of carbocation intermediate.

31
Q

why is sterochemistry retained in hydroBORation (BH3) addition?

A

because they make that weird square transition intermediate thing instead of carbocation intermediate.

32
Q

do bromination addition rxns make carbocation intermediates or weird triangle intermediates?

A

weird triangle intermediates (called bromonium ion)

33
Q

why don’t we have to care about regioselectivity (substituted-ness) in bromination addition rxns?

A

because you’re adding 2 of the same thing across the double bond.

34
Q

why do we have to care about stereochemistry in bromination addition rxns?

A

because adding the Br creates chiral centers

35
Q

do bromination addition rxns do anti addition or syn addition?

A

anti;

the weird triangle intermediate (bromonium ion) can only be attacked from behind

36
Q

what is the difference between the bromination addition (Br2) and the halohydrin addition rxn (Br & OH)?

A

Br2 adds Br accross the double bond in anti addition

Br & OH adds Br on one side of double bond, and OH on the other (more substituted) side of double bond

37
Q

do bromination addition rxns and halohydrin addition rxns do rearrangement?

A

No. Both of these make the weird transition shape instead of a carbocation intermediate.

38
Q

do halohydrin addition rxns do anti addition or syn addition?

A

anti

39
Q

what’s the difference between the substrates for bromination addition rxns and halohydrin addition rxns?

A

bromination addition rxns (Br2) only has Br2

halohydrin addition rxns has Br2 AND H2O

40
Q

can bromination addition rxns and halohydrin addition rxns use other halogens besides Br2?

A

Yes

bromination addition rxns that use Cl2 instead of Br2 are called halogenation

halohydrin addition rxns can use Cl2, too, but without the name change

41
Q

what gets added across the double bond in a dihydroxylation addition rxn?

A

two OHs

42
Q

when do dihydroxylation addition rxns do anti addition?

A

when substrates are:

Step 1: RCO3H (peroxyoxide)

Step 2: H3O+

43
Q

when do dihydroxylation addition rxns do SYN addition?

A

when substrates are:

Step 1: OsO4 (osmium tetraoxide)
Step 2: NaHSO3, H2O

OR

Step 1: KMNO4 (Potassium permanganate)
Step 2: H2O, OH-

44
Q

do dihydroxylation addition rxns make carbocation intermediates/do rearrangement?

A

no.

They make epoxide intermediates instead of carbocation intermediates.

45
Q

do dihydroxylation addition rxns do syn addition or anti addition?

A

either one, depending on your substrates

46
Q

what does oximercuration-dermurcuration addition add across the double bond?

A

H and OH

47
Q

does oximercuration-dermurcuration addition do mark or anti-mark addition?

A

mark

48
Q

does oximercuration-dermurcuration addition do mark or anti-mark addition?

A

mark

49
Q

why doesn’t oximercuration-dermurcuration addition do rearrangement?

A

bc it makes the weird intermediate instead of the carbocation intermediate

50
Q

what reagents are needed for oximercuration-dermurcuration addition rxns?

A

step 1: Hg(OAc)2 mercury (II) acetate and the nucleophile; usually water
step 2: NaHB4

51
Q

what happens during ozonolysis/oxidative cleavage rxns?

A

the electrophile’s double bond is completely broken, leaving you with two carbonyls in its place

52
Q

are ketones and aldehydes two types of carbonyls?

A

yes

53
Q

what are the 2 types of carbonyls you can get as products in an ozonolysis/oxidative cleavage rxn?

A

ketones and aldehydes

54
Q

do ozonolysis/oxidative cleavage rxns involve rearrangement?

A

yes!

55
Q

what reactants are involved in ozonolysis/oxidative cleavage rxns?

A

O3, Zn, and H2O

OR

O3 and CH3SCH3

56
Q

in a ozonolysis/oxidative cleavage rxn, what do you get for every double bond you break?

A

two carbonyls

57
Q

in ozonolysis/oxidative cleavage rxns, what do you get for every C to C double bond that you break?

A

2 carbon to oxygen bonds

58
Q

what is the carbon connected to in a ketone

A

carbon has:
one double bond to an oxygen
one single bond to a R group
another single bond to another R group

59
Q

what is the carbon connected to in a aldehyde?

A

carbon has:
one double bond to an oxygen
one single bond to a R group
one single bond to a HYDROGEN

O Chem II CSCC (14 decks)

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