Quiz 1 Flashcards

1
Q

how do you produce a compound with just single bonds from a terminal alkyne

A

H2, Pd/C

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2
Q

how do you produce a compound with X on the most substituated carbon and a double bond on the terminal position from a terminal alkyne

A

HX where X = Cl, Br, or I

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3
Q

how do you produce a compound with only single bonds and two Xs located on the same carbon from a terminal alkyne

A

xs HX

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4
Q

how do you produce a compound with a double bond on the terminal position and one X is on one of the double bonded carbons, while the other X is on the other double bonded carbons from a terminal alkyne

A

Br2 or Cl2

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5
Q

how do you produce a compound with just single bonds and two Xs on one carbon and two Xs on the other carbon from a terminal alkyne

A

xs Br2 or Cl2

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6
Q

how do you produce a compound with the triple bond and a new R group formed from a terminal alkyne

A
  1. NaNH2
  2. RCH2Br
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7
Q

how do you produce an aldehyde (double bond on oxygen) from a terminal alkyne

A
  1. 9-BBN
  2. H2O2, HO-
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8
Q

how do you produce a ketone from a terminal alkyne

A

H2O, H2SO4

HgSO4

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9
Q

how do you reduce a compound from a triple bond to a double bond for a terminal alkyne

A

H2

Lindlar catalyst

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10
Q

how do you produce a compound with just single bonds from a internal alkyne

A

H2, Pd/C

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11
Q

how do you produce a ketone from an internal alkyne

A
  1. BH3
  2. H2O2, HO-
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12
Q

how do you produce a compound with an internal double bond and an X on one of the double bond carbons, while the other X is on the other double bonded carbon from an internal alkyne

A

Br2 or Cl2

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13
Q

how do you produce a compound with just single bonds and two Xs on one carbon and two Xs on the other from a internal alkyne

A

xs Br2 or Cl2

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14
Q

how do you produce a compound with an internal double bond and an X bonded to one of the carbons from an internal alkyne

A

HX

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15
Q

how do you produce a compound with just single bonds and two Xs bonded to one internal carbon from an internal alkyne

A

xs HX

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16
Q

how do you produce a cis alkene from a internal alkyne

A

H2

Lindlar catalyst

(syn addition)

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17
Q

how do you produce a trans alkene from an internal alkyne

A

Na or Li, NH3

(anti addition)

18
Q

how to turn a terminal alkyne to an internal alkyne

A

adding the group you want (THE TRIPLE BOND STAYS AS A TRIPLE BOND)

  1. NaNH2
  2. RCH2Br
19
Q

how to turn an internal alkyne to a terminal alkene

A

ozonolysis: cuts the double bond in half and puts an oxygen on the double bond, turning it into a aldehyde

  1. O3
  2. Zn, CH3CO2H
20
Q

what is acetylene

A

H-C triple bond C-H

21
Q

how do you produce a compound with just single bonds and an OH bonded to an internal carbon from a terminal alkene

A

H2O, H2SO4

22
Q

how do you produce a compound with just single bonds and an OH bonded at the end from a terminal alkene

A
  1. BH3
  2. H2O2, HO-
23
Q

how do you produce a compound with just single bonds and an X bonded to an internal carbon, and another X bonded to the other carbon from a terminal alkene

A

Br2 or Cl2

24
Q

how do you produce a compound with just single bonds and an OH bonded to an internal carbon, and another X bonded to the other carbon from a terminal alkene

A

Br2 or Cl2

H2O

25
Q

Characteristics of a triple bond

A
  • bond angle of 180 degrees
  • short carbon carbon bond of 120 A (very short)
  • strong bond of 231 kcal/mol (very strong)
26
Q

rank the stability of carbocations from MOST to LEAST stable

A

Most
- tertiary carbocation
- secondary carbocation
- secondary vinylic cation (ab the same stability as the next one)
- primary carbocation
- primary vinylic cation (about the same stability as the next one)
- the methyl cation
Least

27
Q

dihalide vs. tetrahalide

A

dihalide: one halide (Br or Cl) group

tetrahalide: two halides on one carbon (AKA geminal)

28
Q

why do two halides end up on the same carbon?

A

to improve stability (e- sharing)

29
Q

keto-enol tautomerism

A

to produce a ketone, an enol is formed first (instead of an O double bond, it has an OH group), but the enol is nearly impossible to isolate.

30
Q

tautomerism

A

are structural isomers (constitutional isomers) of chemical compounds that readily interconvert (differ by the location of a double bond and a hydrogen atom)

31
Q

internal vs. terminal for need of a catalyst or not and why

A

internal: no need for a catalyst

terminal: needs a catalyst to help it get over the activity threshold since it’s not as e- rich (the more alkyl groups present, the more e- they can donate). Terminal alkynes are also less reactive.

32
Q

why is a trans product produced?

A

because 9-BBN is so big it creates steric repulsion (the bulky groups go on opposite sides)

33
Q

high pKa vs. low pKa

A

low pKa = easy to remove proton (stronger acid)

high pKa = difficult to remove proton (stronger base)

34
Q

ethyne pKa (HC triple bond HC)

A

25

35
Q

ethene pKa (H2C=CH2)

A

44

36
Q

ethane pKa (CH3CH3)

A

greater than 60

37
Q

why is the stability like this: alkyl group (sp3 hybridized) (least stable), a vinylic group (sp2 hybridized), and acetylide anion (sp hybridized) (most stable)

A

alkyl groups: 25 % s character
vinylic groups: 33 % s character
acetylide anion: 50 % s character

38
Q

pKa of H2O

A

15.7

39
Q

pKa of HF

A

3.2

40
Q

pKa of NH3

A

36