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Medicinal Chemistry > Functional Group Chemistry 2 > Flashcards

Functional Group Chemistry 2 Flashcards

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1
Q

Describe alkanes

A

Saturated = single bonds = sigma
CnH2n+2
pKa > 50

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2
Q

What are the properties of alkanes?

A

Poorly reactive with ionic or polar substances
Inert to acids + bases
Virtually insoluble to H2O

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3
Q

What happens to boiling point as size of alkanes increase?

A

Increase

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4
Q

What are alkanes used for?

A

Fuels

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5
Q

Describe intermolecular forces of alkanes

A

Weak = no difference in electronegativity = no dipoles

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6
Q

Describe alkenes

A

Unsaturated = pi bonds
Double bond = slightly polar
CnH2n

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7
Q

What is reactivity controlled by in alkenes?

A

How e- rich the double bond is = act as nucleophile

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8
Q

What does it mean the pi bond in alkenes is polarizable?

A

= instantaneous dipole-dipole interactions occur

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9
Q

What do the conversion of alkene isomers require?

A

Breaking of pi bond between 2x sp2 carbons

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10
Q

How do you get from alkene cis to trans?

A

180 degrees

UV light

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11
Q

What is cis?

A

Same side

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12
Q

What is trans?

A

Opposite

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13
Q

What happens when C=C is broken to C-C?

ISOMERS

A

C=C reformed to form more stable orbitals

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14
Q

What is the preparation methods for alkenes?

A

Cracking

Elimination reactions of halides/alcohols

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15
Q

What can alkenes form?

A 
Haloalkanes
Alcohols
Vicinal dihaloalkanes
Alkanes
Polymers
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16
Q

What is addition reactions via for alkenes?

A

Electrophilic addition

17
Q

Where does e- move in alkenes?

A

From double bond to electrophilic centre

18
Q

What can addition reactions be?

A

Homolytic (involves radicals)

Heterolytic (involves cations)

19
Q

Describe reactivity of C=C

A

Pi e- attack E+ (heterolytic) or radical intermediate (homolytic)
Nu- adds to carbocation/radical

20
Q

Describe addition of halogens to alkenes

A

Cl2, Br2 + I2 add to C=C to form vicinal dihalide

Anti or trans addition = stereospecific reaction

21
Q

Describe addition of bromine to alkenes

A

Red/brown colour goes colourless upon reaction

Br- = Nu-

22
Q

Describe addition of H-X to alkenes

A

Symmetrical alkene = 1 product

Unsymmetrical = 2 different products

23
Q

Describe anti-Markovnikov addition to alkenes

A

Peroxides present = HBr adds to alkenes to form “Anti-Markovnikov” product through radical mechanism
Only HBr has right bond energy

24
Q

Describe anti-Markovnikov addition to alkenes stages

A

Initiation + propagation = Br2 adds to sterically least hindered C
Radical cleaves HBr in 2nd propagation
= radical chain
Termination = contamination

25
Q

Describe hydrogenation in alkenes

A

Form alkane
Syn or Cis addition
Reaction = stereospecific
Catalyst required = Pt, Pd or Ni

26
Q

Describe alkynes

A 
Unsaturated 
Triple bonds
Reactivity dominated by reactive e- rich triple bond 
CnH2n-2
pKa = 44
27
Q

What are the properties of alkynes?

A

Virtually insoluble to H2O
Stronger Van Der Waals
Internal alkenes/alkynes have higher boiling points than terminal

28
Q

Describe electronegativity of orbitals

A

sp > sp2> sp3
sp = most
sp3 = least

29
Q

What happens to acidity as s-orbital character increases?

A

Increases

30
Q

Describe alkyne reactivity

A

Completely burn in O2

31
Q

What reactions do alkyne undergo?

A 
H-X addition
With/without peroxides 
X-X addition (Br2, Cl2)
Hydrogenation 
H-OH (hydration)
Alkylation of terminal alkynes
32
Q

Describe addition of HX to alkynes

A

Follows Markovnikov rule
Vinylic carbocations in 1st step

Triple bond compose of sigma bond + 2x pi bonds
Pi bond broken = new sigma bonds formed
2nd addition

33
Q

What are the alkyne addition reaction?

A 
Halogenation = same as alkenes
Anti-Markovnikov = needs peroxide
34
Q

Describe addition of H2O to alkynes

A

Same as alkenes

Acid catalysed

Medicinal Chemistry (19 decks)

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