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Medicinal Chemistry > Functional Group Chemistry 3 > Flashcards

Functional Group Chemistry 3 Flashcards

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1
Q

Describe alcohols

A

Unsaturated or saturated
O = sp3
Act as Nu-
Reactivity controlled by e- rich O

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2
Q

What happens to alcohol boiling point as homologous sequence increases?

A

Increases

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3
Q

Why do alcohols have unusually high boiling points?

A

H bonding

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4
Q

What happens to solubility of alcohols as size of alkyl group increases?

A

Decreases

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5
Q

What is the pKa range of alcohols?

A

15.5-18.0

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6
Q

What happens to acidity of alcohols as alkyl group increases?

A

Decreases

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7
Q

What do halogens do to alcohols?

A

Increase acidity = e- withdrawal

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8
Q

What is the preparation of alcohols?

A

CO + 2H2 —-> CH3OH
400 degrees
ZnO/CrO3

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9
Q

What are the 3 main ways more complex alcohols are formed?

A

Hydration of alkenes
Hydrolysis of alkyl halides
Reduction of aldehydes/ketones/esters

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10
Q

What can the aldehyde be reduced to?

A

Primary alcohol

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11
Q

What can a carboxylic ester be reduced to?

A

Primary alcohol

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12
Q

What can a carboxylic acid be reduced to?

A

Primary alcohol

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13
Q

What is a ketone reduced to?

A

Secondary alcohol

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14
Q

What are aldehydes and ketones reduced by?

A

Sodium borohydride = NaBH4
OR
Lithium aluminium hydride = LiAlH4

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15
Q

What can acids + esters only be reduced by?

A

LiAlH4

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16
Q

How can alkoxides be formed?

A

React ethanol with sodium metal (redox reaction)
OR
Cleavage of haloalkanes by hydroxide
Conversion to haloalkanes

17
Q

Describe addition of H-X to alcohols

A

HCl, HBr or HI
Displaces hydroxyl with halogen
Form haloalkane

18
Q

How is an ester formed from an alcohol?

A

Acid + alcohol ⇆ ester + H2O

H+ catalyst = H2SO4

19
Q

What is the equation for acid dehydration?

A

Acid + alcohol ⇆ ester + H2O

20
Q

What is the equation for acid hydrolysis?

A

Ester + H2O ⇆ acid + alcohol

21
Q

What are alcohols oxidised to?

A

Aldehydes —-> carboxylic acids

Ketones

22
Q

What is needed for alcohol oxidation?

A

Metal salts

23
Q

Describe phenols

A

Planar
C-O bond distance shorter
Unusual H bonding

24
Q

What does the hydroxyl group of phenols allow?

A

H bonding to other phenol molecules in H2O

25
Q

What does the H bonding in phenols do?

A

Raises melting point

Increases solubility in H2O

26
Q

What is phenoxide stabilised by?

A

Resonance

27
Q

What do phenols have compared to alcohols?

A

Higher acidity

28
Q

Describe haloalkanes

A

Act as E+
Reactivity controlled by e- poor C
C can be attacked by Nu-
Halogen can leave with e- pair

29
Q

What does it mean that the C-halogen bond is polar?

A

Bonded C has partial positive charge

30
Q

What does a haloalkane have compared to alkane?

A

Higher boiling point

= greater polarizability of C-X bond

31
Q

What is the density of liquid haloalkanes compared to hydrocarbons?

A

Higher

32
Q

How are haloalkanes prepared?

A

Free radical substitution of alkanes
Electrophilic addition to alkenes
Halogenation of alcohols
Halogenation of alkenes/alkynes

33
Q

Describe nucleophilic substitution of haloalkanes

A

Alkyl halides polarised at C-X bond = C electrophilic

Nu- replaces halide in C-X bond

Medicinal Chemistry (19 decks)

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