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S1 - Medicinal Chemistry > Functional Groups > Flashcards

Functional Groups Flashcards

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1
Q

Why are alkanes known as paraffins ?

A
  • due to unreactivity
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2
Q

What state are alkanes ?

A
  • CH4 to C4H10 are gases
  • C5H12 to C17H36 are liquids
  • C18H38 and above are solids
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3
Q

Why does bp of Alkanes increase as chain length increases ?

A
  • More London forces
  • more surface points of contact
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4
Q

what is an electrophile ?

A
  • electron lover
  • accepts a pair of electrons
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5
Q

what is a nucleophile ?

A
  • donates a pair of electrons
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6
Q

what is the HOMO?

A
  • highest occupied molecular orbital
  • nucleophile has pair of e- in the HOMO
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7
Q

what is the LUMO ?

A
  • low energy anti-bonding orbitals
  • lowest unoccupied molecular orbitals
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8
Q

what does a curly arrow represent ?

A
  • movement of a pair of electrons from a filled orbital into an empty one
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9
Q

What is the difference between SN1 and SN2 mechanisms ?

A
  • SN1 - leaving group goes first , carbocation produced and then nucleophile attacks
  • SN2 - nucleophile attacks same time as leaving group goes so no carbocation
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10
Q

what 3 things does rate of an Sn2 reaction depend on ?

A
  • nucleophile
  • carbon skeleton
  • the leaving group

also temp + solvent

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11
Q

what 2 factors does rate of Sn1 reaction depend on ?

A
  • carbon skeleton
  • the leaving group

temp + solvent

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12
Q

what is the RDS (rate-determining step) in Sn1?

A
  • formation of carbocation
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13
Q

How does structure of carbon skeleton affect Sn1 reaction ?

A

methyl + 1°= no cause unstable carbocation
2° = moderate, slower than 3°
3° = fastest very stable cation

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14
Q

How does structure of carbon skeleton affect Sn2 reaction ?

A

methyl + 1°= fastest due to low steric hindrance
2° = moderate some steric hindrance
3° = no, high steric hindrance

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15
Q

what is steric hinderance ?

A
  • slowing down of a chemical reaction due to bulk of other groups
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16
Q

How does steric hinderance affect Sn1 reactions ?

A
  • stabilises carbocation
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17
Q

how does steric hinderance affect Sn2 reactions ?

A
  • low steric hinderance easy for nucleophile to attack
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18
Q

what is a racemic mixture and how does it form in Sn1 reactions ?

A

Racemic -contains equal amounts of 2 enantiomers.
- in sn1 - when a chiral carbon forms a carbocation , nucleophile can attack from both sides

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19
Q

what is a polar protic solvent ?

A
  • can form H bonds
    eg. water, alcohol
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20
Q

what is an aprotic solvent ?

A
  • cannot form H bonds
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21
Q

does sn1 take place in protic or aprotic solvents ?

A
  • protic because they stabilise carbocation
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22
Q

does sn2 take place in protic or aprotic solvents ?

A
  • apotric
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23
Q

how is the stereochemistry inverted in Sn2 ?

A
  • nucleophile attacks from backside , side oppsodie to the one where leaving group goes
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24
Q

Does the double bond in Alkenes act as a nucleophile or electrophile ?

A
  • nucleophile
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25
Q

How does conversion of alkene isomers occur ?

A
  • breaking of pi bond
  • eg. cis to trans conversion
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26
Q

What are the 2 methods of preparing alkenes ?

A
  • cracking
  • elimination of halides/alcohols or
27
Q

how does cracking produce alkenes ?

A
  • long chain alkanes are cracked to form a alkene and smaller alkane
28
Q

When does anti - markovinikov addition occur?

A

’ Presence of peroxides

29
Q

What are alkynes?

A
  • Contains triple c-c bonds - 2 pi and 1 sigma bond
30
Q

What is a stereospecific reaction ?

A
  • stereochemistry of reactant determines stereochemistry of product
31
Q

what is a diastereoisomer ?

A

-non- mirror images

32
Q

what is the bromonium ion and is it an electrophile or nucleophile ?

A
  • Br+
  • electrophile
33
Q

What is the inductive effect ?

A
  • electron withdrawing groups (electronegative ) pull e- towards themselves through sigma bond
  • electron donating groups (alkyl) push e- density onto positively charged center
34
Q

Why is tertiary carbocation more stable than primary ?

A
  • greater number of alkyl groups
  • more carbons = increased positive inductive effect
35
Q

What conditions are needed for anti-markovnikovs rule ?

A
  • peroxide
  • hydrogen bromide
36
Q

Difference between anti and normal markovnikovs?

A
  • anti uses radicals not carbocations
  • in anti- H attaches to C with fewer H’s
  • wheras in normal it attaches to one with most H’s
37
Q

stages of anti-markovnikov addition

A
  • initiation - RO–O–R→2RO*
  • propagation - RO+HBr→ROH+Br
    Br* adds to the less substituted carbon of the alkene, creates a new alkyl radical on the more substituted carbon of the alkene.

termination = Br+Br→Br2
alkylradical+Br*→bromoalkane

38
Q

conditions for hydrogenation of alkenes

A
  • 150c
  • Ni,pt,pd (palladium) catalyst
39
Q

which hybridsation of carbon is more electronegative ?

A

sp>sp2>sp3

40
Q

what does tautomerisation of alkynes form ?

A

alkyne —> enol —-> ketone

41
Q

what is an enol ?

A
  • alkene with an OH group
42
Q

How are haloalkanes prepared ?

A
  • radical substitution of alkanes
  • halogenation of alcohols
  • electrophilic addition of alkenes
43
Q

What happens to acidity as alkyl group increases (positive inductive effect)?

A
  • Acidity decreases as alkyl group increases
44
Q

What effect does negative inductive effect have on acidity ?

A
  • increased acidity
45
Q

What are 3 methods of preparing alcohols ?

A
  • hydration of alkenes
  • reduction of aldehydes and ketones
  • hydrolysis of haloalkanes
46
Q

reduction of aldehydes and ketones ?

A
  • reduced by NaBH4 or LiAlH4 - acts as H- source
  • aldehydes reduced to 1° alcohol
  • ketone reduced to 2° alcohol
47
Q

what is an alkoxide ion and how is it formed ?

A
  • deprotination of OH
  • R−O-
48
Q

how are esters formed ?

A
  • carboxylic acid + alcohol —–> ester
  • in presence of acid catalyst
49
Q

oxidation of alcohols ?

A
  • 1° alcohol –> aldehyde –> carboxyllic acid
  • acidified potassium dichromate
  • 2° alcohol - ketone
50
Q

what is the role of alcohol dehydrogenase ?

A
  • converts alcohol to aldehyde
51
Q

what is the aldehyde dehydrogenase ?

A
  • converts aldehyde to carboxyllic acid
52
Q

what is the shape and hybridisation of phenol ?

A
  • sp2
  • planar
53
Q

is phenol more acidic than alcohols ?

A
  • yes because the phenoxide ion is stabilised by resonance
54
Q

what is the role of the hormone epinephrine ?

A
  • fight or flight response
55
Q

what are primary, secondary, tertiary, amines ?

A
  • primary - 2H
  • secondary - H
  • tertiary - no H’s
56
Q

why are amine salts more soluble compared to amines ?

A
  • amine salts are ionic
  • eg. NH3+Cl-
57
Q

Is a H bond in alcohol or amine stronger

A
  • alcohol because O is more electronegative
58
Q

What is a zwitterion ?

A
  • formed from amino acids
  • have a NH3+ group and COO- group
  • have a pH of 7
59
Q

how are nitriles formed ?

A
  • Alkyl halide + NaCN
60
Q

how are amides formed ?

A
  • Carboxyllic acid + SOCl2 + NH3
61
Q

how are amides formed from amines ?

A
  • Acid chloride (RCOCl) +
    1 or 2 Amine
62
Q

how are sulfonamides made?

A
  • Sulfonyl chloride (R-SO₂Cl) and 1 or 2 amine
63
Q
A

S1 - Medicinal Chemistry (8 decks)

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