Alkynes and cycloalkynes Flashcards

(54 cards)

1
Q

unsaturated hydrocarbons where some hydrogens have been replaced by triple carbon-carbon bonds

A

alkynes

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2
Q

General Formula of alkynes

A

CnH2n-2

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3
Q

Carbons in triple bond are __ __ and have __ geometry

A
  • sp hybridized
  • linear
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4
Q

sp hybridized angle

A

180

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5
Q

sp2 hybridized angle

A

120

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6
Q

sp3 hybridized angle

A

109.5

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7
Q

3 bonds of alkynes

A
  • 1 sigma bond
  • 2 pi bonds
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8
Q

carbon triple bond is __ than carbon double bond

A

stronger

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9
Q

bond length of triple bonds compared to double bonds

A

shorter

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10
Q

__ __ are easy to break. Opening opportunity for reactions

A

unsaturated hydrocarbons

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11
Q

open bonds from the uncoiling of triple and double bonds, the opened bonds could provide connections for carbon atoms to attach to

A

polymerization

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12
Q

How to name alkynes

A
  1. find longest chain with triple bond
  2. start counting closest to triple bond
  3. in presence of alcohol, number starting to closest alcohol
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13
Q

suffix of alkynes with alcohol

A

-ynol

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14
Q

name of alkyne that is a substituent

A

alkynyl (ex. ethynyl)

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15
Q

molecule that contains both double and triple bonds

A

alkenyne

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16
Q

how to number alkenyne

A

starting end closest to the functional group that appears first

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17
Q

simplest form of alkyne

A

acetylene (ethyne)

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18
Q

consist of closed ring of carbon atoms containing one or more triple bonds

A

cycloalkyne

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19
Q

the linear nature of alkyne unit makes cycloalkynes __

A

strained

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20
Q

because of linear nature of alkynes, cycloalkynes are __ __ occuring organic compounds

A

very rare

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21
Q

General Formula of cycloalkynes

A

CnH2n-4

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22
Q

Two types of alkynes

A
  1. terminal
  2. internal
23
Q

a carbon-carbon triple bond at the end of the carbon chain

A

terminal alkynes

24
Q

carbon-carbon triple bond in the middle of the carbon chain

A

internal alkynes

25
boiling point of alkynes compared to other hydrocarbons
higher boiling point
26
electric field of alkynes
more susceptible to distortion
27
why is the electric field of alkynes more susceptible to distorition
due to increased number of weakly held electrons
28
boiling points of alkynes rise in proportion to the
size of molecular structres
29
boiling points of alkynes rise with the increase of
molar mass
30
density of alkynes
- lighter, lower density than water - become more dense as mass increases
31
physical state of alkynes
- odorless, colorless - first three alkynes are gases - next eight alkynes are liquid - all alkynes higher than there are solids
32
physical state: 2-4 carbon alkynes
gases
33
physical state: 5-12 carbon alkynes
liquid
34
physical state: 13 and above carbon alkynes
solid
35
solubility of alkynes
- dissolve in organic solvents - slight solubility in polar solvents - insoluble in water
36
example of non polar organic solvents
- benzene - ether
37
polarity of alkynes
- nonpolar - more electronegative than alkenes and alkanes
38
why are alkynes more electronegative than alkanes and alkenes
due to sp hybridized carbon atom
39
Alkynes: addition reactions
addition across triple bond to form alkanes
40
Different addition reactions of alkynes
1. hydrogenation 2. halogenation 3. hydrohalogenation 4. hydration 5. oxidation 6. polymerization
41
- an addition reaction where hydrogen molecules are used to saturate organic compounds - process is effective under certain catalytic conditions and controlled temperatures depending on the type of hydrocarbon - undergo the same with the same catalysts used in alkene
hydrogenation
42
- involves the reaction of a compound with a halogen and results in the halogen being added to the compound - possible to stop this reaction at alkene stage by runnint it at temperature slightly below 0C
halogenation
43
- When hydrogen halide is treated with alkynes (triple bond compounds) it results in the formation of gem halides. - Gem halides are the compounds in which two halogens are attached to the same carbon atoms in a molecule.
hydrohalogenation
44
compounds in which two halogens are attached to the same carbon atoms in a molecule
Gem halides
45
- addition of water to alkynes - formes aldehydes and ketones
hydration
46
what is formed after hydration of alkynes
- aldehydes - ketones
47
hydration in alkynes
water across triple bond via carbocation mechanism
48
loss of electrons during a reaction by a molecule, atom or ion
Oxidation
49
Alkynes undergo ozonolysis to give
- acid anhydrides or diketonesion - carboxylic acid
50
alkynes can be polymerized by both
- cationic methods - free-radical methods
51
because of the linear shape of alkynes, __ __ does not occur
geometric isomerism
52
- due to the different arrangment of carbon atoms in the chain that is straight-chain or branched
chain isomerism
53
- due to the difference in the location of triple bond
position isomerism
54
- alkynes are isomeric with alkadienes both being represneted by the general formula CnH2n-2
functional isomerism