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O Chem II CSCC > Addition Rxns > Flashcards

Addition Rxns Flashcards

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
does hydroBORation do Markonikov addition or andi-markonikov addition?
anti. It's like hydration (in that it adds water across double bond), but it does anit mark
26
which addition rxns add water across the double bond?
hydration (mark) oximercuration-demercuration (mark) hydroBORation (anti-mark)
27
what happens in a hydroBORation (BH3) addition?
alkene becomes an alcohol: double bond attacks H, then BH2 goes to LESS substituted carbon, then gets replaced by OH
28
what are the reactants for hydroBORation (BH3) addition?
Step 1: BH3, THF Step 2: H2O2, NaOH
29
do hydroBORation (BH3) addition have carbocation intermediates/rearrangement?
no; They make that weird square transition intermediate thing instead of carbocation intermediate.
30
why do hydroBORation (BH3) addition rxn only do syn addition?
because they make that weird square transition intermediate thing instead of carbocation intermediate.
31
why is sterochemistry retained in hydroBORation (BH3) addition?
because they make that weird square transition intermediate thing instead of carbocation intermediate.
32
do bromination addition rxns make carbocation intermediates or weird triangle intermediates?
weird triangle intermediates (called bromonium ion)
33
why don't we have to care about regioselectivity (substituted-ness) in bromination addition rxns?
because you're adding 2 of the same thing across the double bond.
34
why do we have to care about stereochemistry in bromination addition rxns?
because adding the Br creates chiral centers
35
do bromination addition rxns do anti addition or syn addition?
anti; the weird triangle intermediate (bromonium ion) can only be attacked from behind
36
what is the difference between the bromination addition (Br2) and the halohydrin addition rxn (Br & OH)?
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
do bromination addition rxns and halohydrin addition rxns do rearrangement?
No. Both of these make the weird transition shape instead of a carbocation intermediate.
38
do halohydrin addition rxns do anti addition or syn addition?
anti
39
what's the difference between the substrates for bromination addition rxns and halohydrin addition rxns?
bromination addition rxns (Br2) only has Br2 halohydrin addition rxns has Br2 AND H2O
40
can bromination addition rxns and halohydrin addition rxns use other halogens besides Br2?
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
what gets added across the double bond in a dihydroxylation addition rxn?
two OHs
42
when do dihydroxylation addition rxns do anti addition?
when substrates are: Step 1: RCO3H (peroxyoxide) Step 2: H3O+
43
when do dihydroxylation addition rxns do SYN addition?
when substrates are: Step 1: OsO4 (osmium tetraoxide) Step 2: NaHSO3, H2O OR Step 1: KMNO4 (Potassium permanganate) Step 2: H2O, OH-
44
do dihydroxylation addition rxns make carbocation intermediates/do rearrangement?
no. They make epoxide intermediates instead of carbocation intermediates.
45
do dihydroxylation addition rxns do syn addition or anti addition?
either one, depending on your substrates
46
what does oximercuration-dermurcuration addition add across the double bond?
H and OH
47
does oximercuration-dermurcuration addition do mark or anti-mark addition?
mark
48
does oximercuration-dermurcuration addition do mark or anti-mark addition?
mark
49
why doesn't oximercuration-dermurcuration addition do rearrangement?
bc it makes the weird intermediate instead of the carbocation intermediate
50
what reagents are needed for oximercuration-dermurcuration addition rxns?
step 1: Hg(OAc)2 mercury (II) acetate and the nucleophile; usually water step 2: NaHB4
51
what happens during ozonolysis/oxidative cleavage rxns?
the electrophile's double bond is completely broken, leaving you with two carbonyls in its place
52
are ketones and aldehydes two types of carbonyls?
yes
53
what are the 2 types of carbonyls you can get as products in an ozonolysis/oxidative cleavage rxn?
ketones and aldehydes
54
do ozonolysis/oxidative cleavage rxns involve rearrangement?
yes!
55
what reactants are involved in ozonolysis/oxidative cleavage rxns?
O3, Zn, and H2O OR O3 and CH3SCH3
56
in a ozonolysis/oxidative cleavage rxn, what do you get for every double bond you break?
two carbonyls
57
in ozonolysis/oxidative cleavage rxns, what do you get for every C to C double bond that you break?
2 carbon to oxygen bonds
58
what is the carbon connected to in a ketone
carbon has: one double bond to an oxygen one single bond to a R group another single bond to another R group
59
what is the carbon connected to in a aldehyde?
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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