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Mpharm 1 > PH1125 - Organic Functional Groups > Flashcards

PH1125 - Organic Functional Groups Flashcards

1
Q

what is an organic compound?

A
  • any chemical compound that contains carbon
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2
Q

what are carbon containing compounds that are not organic? (2)

A
  • carbonates; -CO3-

- cyanide; -CN

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3
Q

what is an imine?

A
  • a compound with a nitrogen atom double bonded to a carbon atom
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4
Q

what is an azide?

A
  • a compound with -N3
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5
Q

what is a functional group?

A
  • specific substituents or moieties within molecules that are responsible for the characteristic chemical reactions and physical properties of those molecules
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6
Q

what is the polarity and reactivity of alkanes? (4)

A
  • mostly chemically unreactive
  • non-polar
  • not soluble in water; hydrophobic
  • lipophilic
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7
Q

what kind of isomers can compounds with double bonds exist as?

A

E Z isomers

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8
Q

describe the reactivity of alkenes (2)

A
  • reactivity due to their electron rich nature
  • the pi electrons above and below the plane of the C=C double bond are more weakly held than sigma electrons and are therefore more chemically reactive
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9
Q

what is regioselectivity?

A
  • the preference for one orientation over another in the arrangement of a reaction product
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10
Q

why do tertiary carbons have the lowest energy and the highest stability?

A
  • they are stabilised by electron density from all three neighboring carbon atoms
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11
Q

what is markovnikov’s rule? (2)

A
  • in reactions of HX to alkenes the H bonds to the carbon with more hydrogens (fewer substituents)
  • the X bonds to the carbon with more substituents (fewer hydrogens)
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12
Q

what are the pharmaceutical considerations for alkenes as drugs? (4)

A
  • poor water solubility
  • reactive (prone to oxidation) therefore possibility of shorter shelf-life
  • important in medicinal chemistry for the ability to exist as E/Z isomers
  • different isomers have different biological properties
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13
Q

how are alkenes reduced to alkanes? (2)

A
  • hydrogen

- palladium catalyst

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14
Q

what is the product when alkenes are oxidised with potassium permanganate? (2)

A
  • cis-1,2-diols
  • the permanganate adds across the double bond to form an unstable intermediate that reacts with water to generate the diol
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15
Q

what is the alternative oxidising agent to make trans-1,2-diols? (2)

A
  • peroxides

- the peroxyacid converts the alkene into an epoxide that reacts with water on the opposite side of the ring

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16
Q

what does the reaction of ozone and alkenes make? (2)

A
  • involves breaking the double bond

- alkenes are converted into carbonyl compounds

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17
Q

what are the two principle methods for synthesizing alkenes? (2)

A
  • alcohol dehydration

- wittig reaction

18
Q

what is an alkyne functional group?

A
  • carbon-carbon triple bond
19
Q

what is the hybridization present in alkynes and shape?

A
  • sp hybridized carbon atoms

- linear geometry; 180

20
Q

what are the physiochemical properties of alkynes? (4)

A
  • rigid, non-rotatable, linear geometry where E/Z isomers are not possible
  • lipophilic (non-polar) therefore with poor water solubility
  • rich in pi electrons and therefore chemically reactive
  • rare in nature but useful in pharmaceuticals
21
Q

how are alkynes reduced to alkanes? (3)

A
  • hydrogen
  • palladium catalyst
  • alkyne -> alkene -> alkane
22
Q

what does the term ‘poisoning’ refer to?

A
  • reduced reactivity
23
Q

what is cis-hydrogenation?

A
  • both H atoms add to the same side of the double bond
24
Q

how are alkynes reduced to E-alkenes? (2)

A
  • sodium

- in liquid ammonia

25
Q

what do terminal alkynes have?

A
  • C≡C-H terminal H atoms which is slightly acidid
26
Q

what is the relationship between pKa and acidity?

A
  • larger the pKa value the weaker the acid
27
Q

what are the physicochemical properties of haloalkanes? (3)

A
  • generally chemically reactive
  • very useful in organic chemistry but limited use in pharmaceutics
  • lipophilic therefore poor water solubility
28
Q

what is a nucleophile?

A
  • electron rich species than seeks an electron poor site (electron pair donor)
29
Q

as you go down the halogens in haloalkanes (fluorine to chlorine etc) does polarity increase or decrease?

A
  • polarity decreases
30
Q

what is the shape and hybridisation of alcohols? (2)

A
  • 109.5 tetrahedral

- sp3 hybridisation

31
Q

what makes alcohols good nucleophiles?

A
  • lone pairs on the O
32
Q

why are alcohols soluble in water? (2)

A
  • they are polar as oxygen is electronegative and creates a permanent dipole
  • this means it can form hydrogen bonds with water
33
Q

what is an alkoxide?

A
  • conjugate base of an alcohol (salt formed from alcohols and strong bases)
34
Q

why cant alkoxides be used in drug molecules?

A
  • they are too reactive and react readily with water to return to the parent alcohol
35
Q

how are alcohols converted to alkenes (and what kind of reaction is it)? (2)

A
  • in the presence of strong acids

- water is removed and it is a dehydration reaction

36
Q

how are primary alcohols converted to aldehydes? (2)

A
  • oxidisation

- manganese diodide is a mild oxidising agent

37
Q

what is an example of a strong oxidising agent?

A
  • sodium/potassium dichromate (Na2Cr2O7 / K2Cr2O7)
38
Q

what is an alpha hydrogen? (2)

A
  • hydrogen connected to the alpha carbon

- the alpha carbon is the carbon connected to the function group

39
Q

why can’t tertiary alcohols be oxidised?

A
  • they do not contain an alpha hydrogen
40
Q

what is the ether functional group?

A
  • R-O-R
41
Q

are ethers polar?

A
  • they are non-polar
42
Q

how are ethers synthesized? (2)

A
  • primary alcohols are converted to ethers by acid-catalyzed dehydration reactions
  • alkoxides and alkyl halides

Mpharm 1 (59 decks)

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