Chapter 9 Flashcards

1
Q

dehydrogenation

A

name given to an E2 reaction of an alkyl halide. A strong base removes a hydrogen and halogen to get a pi bond.

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2
Q

vicinal

A

on the same side of the molecule (1,2)
(in the vicinity of each other)

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3
Q

geminal

A

on the same carbon (1,1)
(gemini - twins)

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4
Q

double dehydrohalogenation

A

two reactions occur to make an alkyne

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5
Q

when you have a geminial dihalide what do you need to ensure during a double dehydrohalogenation?

A

that there are 2 hydrogens to move

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6
Q

terminal alkynes can be deprotonated with a strong base usually ________ or ________ to create strong nucleophiles called sodium alkynide

A

NaH or NaNH2

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7
Q

terminal alkyne

A

a triple bond with a hydrogen on the end, they are uniquely acidic due to the hybridization effect

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8
Q

is a carbonyl carbon an electrophile?

A

yes! the carbon is positive and the oxygen is negative

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9
Q

nucleophilic addition

A

a carbonyl carbon reacts to make a substituted alcohol

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10
Q

hydrogenation of alkynes

A

there are three methods commonly used to saturate double and triple bonds

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11
Q

hydrogenation of alkynes: full saturation

A
  • hydrogenation (H2 / Ni, Pd, or Pd-C)
  • Wilkonson’s catalyst (H2 / Rh(PPh3)3Cl)
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12
Q

hydrogenation of alkynes: partial saturation

A
  • dissolving metal reduction
  • lindlar’s catalyst
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13
Q

in the hydrogenation of alkynes, in partial summation, what type of stereochemistry does a dissolving metal reduction product have?

A

anti addition (trans product)

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14
Q

in the hydrogenation of alkynes, in partial summation, what type of stereochemistry does a lindlar’s catalyst product have?

A

syn addition (cis products)

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15
Q

alkyne halogenation: product

A

tetrahalide

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16
Q

alkyne hydrohalogenation

A

alkynes react with some addition reagents IN EXCESS to produce double addition products

17
Q

vinyl carbocations

A

the + is directly on the double bond and cannot easily rearrange

18
Q

alkyne hydrohalogenation: product

A

markovnikov gem-dihalide

19
Q

vinyl alcohols are uniquely reactive due to a phenomenon called _____________________

A

tautomerization

20
Q

another name for the intermediate of a vinyl alcohol

20
Q

tautomerization

A

they reversibly swap the positions of a hydrogen and a pi bond

21
Q

another name for the product of alkyne hydration

22
Q

alkyne hydroboration: product

23
Q

alkyne hydroboration: mark or anti-mark OH

A

anti-mark OH

24
oxymercuration of alkynes: mark or anti-mark OH
mark
25
alkyne oxidative cleavage =
carboxylic acid and carbon dioxide
26
when naming molecule with an alkene and alkyne (enyne) where do you start numbering?
start neared to the first multiple bond, whether alkene and alkyne
27
how do you write the root when you have an alkene and alkyne within the molecule?
root-#-ene-#-yne
28
what is the most common alkyne?
H-C-(triple bond)-C-H
29
what occurs when an alkyne is catalyzed with a poisoned catalyst?
cannot continue to reduce so it will end with a double bond
30
when triple bonds have cleaving reactions what are the products?
carboxylic acids
31
when double bonds have cleaving reactions what are the products?
ketones
32
when alkynes react with KMnO4 (cold) what are the products?
double bonded O's replace the triple bond
33
when alkynes react with KMnO4 (hot) what are the products?
double bonded O with OH to replace the double bond