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1
Q

base strength of amines

A

Aliphatic Amines (non-aromatic)

  • Base strength depends on “availability” of the lone pair of electrons
  • Alkyl groups are “electron-donating”.
  • They increase the electron-density around the N atom
  • More likely to gain an electron
  • 1° & 2° amines are better bases than ammonia (3° amines are too crowded)

Aromatic Amines

  • Less basic than aliphatic amines
  • The lone pair of electrons on the N participate in the resonance stabilization of the ring (so are not as available)
1
Q

Aliphatic Amines (non-aromatic)

  • Base strength depends on “availability” of the lone pair of electrons
  • Alkyl groups are “electron-donating”.
  • They increase the electron-density around the N atom
  • More likely to gain an electron
  • 1° & 2° amines are better bases than ammonia (3° amines are too crowded)

Aromatic Amines

  • Less basic than aliphatic amines
  • The lone pair of electrons on the N participate in the resonance stabilization of the ring (so are not as available)
A

base strength of amines

1
Q

these are not basic, the unshared pair of electrons on the Nitrogen is delocalized

  • two resonance forms are possible
  • so, the electrons on the Nitrogen are not “available” to be donated
  • and, amides are less reactive than other carboxylic acid derivatives (esters)
  • also, the geometry of amides is (almost) planar
A

Amides basicity

2
Q

propionamide

A

common name for 3 C chain amide

2
Q

amine toxicity

A

Irritating to skin, eyes, mucous membranes

Some aromatic amines can be absorbed through the skin

2
Q

common name for 5 C chain amide

A

valeramide

2
Q

biologically active amines.

heterocyclic rings

members of the xanthine family

  • Central Nervous System stimulant
  • Bronchodilator (dilates bronchi)
  • Vasodilator (dilates BV)

Diuretic

A

caffeine and theobromine (chocolate) and theophylline

2
Q

1° & 2° amides have the Highest Boiling Points!

  • only the smallest amide is a liquid at RT
  • the rest are solids at RT
  • amides can form intermolecular Hydrogen-bonds
  • intermolecular H-bonding in amides is stronger than in amines
  • the neighboring carbonyl is electron-withdrawing. this makes the N-H bond very polar, so more likely to form H-bonds with the electron pair on the Nitrogen of another amide (or with the Oxygen of water, etc.)
A

amides boiling point

4
Q

common name for 1 C chain amide

A

formamide

5
Q

Irritating to skin, eyes, mucous membranes

Some aromatic amines can be absorbed through the skin

A

amine toxicity

6
Q

formamide

A

common name for 1 C chain amide

8
Q

amine substituent

A

amino group

10
Q

Lewis base

A

unshared electron pair on N can be donated. amines are this.

e.g. ammonia

11
Q

2nd lowest. lower than alcohols and higher than alkanes/alkenes/alkynes

A

amine priority

12
Q

held together via amide linkages

types: nylon, kevlar, polyuretane and proteins

A

polymers

13
Q

amine priority

A

2nd lowest. lower than alcohols and higher than alkanes/alkenes/alkynes

13
Q

aliphatic amines

A

non aromatic amine

14
Q

type of heterocyclic ring

affects CNS

A

nicotine

16
Q

common name for 2 C chain amide

A

acetamide

17
Q

Amines react with acids to produce these

e.g. CH3-NH3+ Cl-

A

amine salts

(ammonium salts)

19
Q

amide

A

a carboxylic acid derivative where carboxyl OH group has been replaced with an amino or substituted amino group

20
Q

nicotine

A

type of heterocyclic ring

affects CNS

21
Q

•– lower than corresponding alcohols

-amines can Hydrogen-bond with other amine molecules

® but N-H bonds are weaker than O-H bonds

A

amine boiling point

22
Q

organic derivative of ammonia NH3 where one or more alkyl, cycloalkyl or aryl groups have replaced ammonia hydrogen atoms

sp3 trigonal pyramidal geometry

A

amine

23
Q

common name for 3 C chain amide

A

propionamide

24
Q

in hemoglobin

carries iron which carries oxygen in blood

A

heme

25
Q

amine smell

A

many have ammonia-like odors or smell of raw fish

27
Q

a carboxylic acid derivative where carboxyl OH group has been replaced with an amino or substituted amino group

A

amide

27
Q

Amine bases in DNA and RNA

A

Adenine, Guanine

Thymine, Cytosine, Uracil

types of heterocyclic rings

28
Q

butyramide

A

common name for 4 C chain amide

29
Q

amides solubility

A

•form strong Hydrogen-bonds with water

  • 1° amides can form 4 Hydrogen-bonds with water
  • water-soluble
30
Q

acetamide

A

common name for 2 C chain amide

32
Q

simplest aromitic amide.

A

benzamide

33
Q

amine boiling point

A

•– lower than corresponding alcohols

-amines can Hydrogen-bond with other amine molecules

® but N-H bonds are weaker than O-H bonds

34
Q

aromatic amines

A

parent compound is aniline

35
Q

non aromatic amine

A

aliphatic amines

36
Q

caffeine and theobromine (chocolate) and thephylline

A

biologically active amines.

heterocyclic rings

members of the xanthine family

  • Central Nervous System stimulant
  • Bronchodilator (dilates bronchi)
  • Vasodilator (dilates BV)

Diuretic

37
Q

Amides basicity

A

these are not basic, the unshared pair of electrons on the Nitrogen is delocalized

  • two resonance forms are possible
  • so, the electrons on the Nitrogen are not “available” to be donated
  • and, amides are less reactive than other carboxylic acid derivatives (esters)
  • also, the geometry of amides is (almost) planar
38
Q

acidic hydrolysis of amide

A

acidic conditions convert amide to carboxylic acid and amine salt

39
Q

parent compound is aniline

A

aromatic amines

40
Q

polymers

A

held together via amide linkages

types: nylon, kevlar, polyuretane and proteins

41
Q

heme

A

in hemoglobin

carries iron which carries oxygen in blood

42
Q

benzamide

A

simplest aromitic amide.

43
Q

many have ammonia-like odors or smell of raw fish

A

amine smell

44
Q

amides boiling point

A

1° & 2° amides have the Highest Boiling Points!

  • only the smallest amide is a liquid at RT
  • the rest are solids at RT
  • amides can form intermolecular Hydrogen-bonds
  • intermolecular H-bonding in amides is stronger than in amines
  • the neighboring carbonyl is electron-withdrawing. this makes the N-H bond very polar, so more likely to form H-bonds with the electron pair on the Nitrogen of another amide (or with the Oxygen of water, etc.)
45
Q

unshared electron pair on N can be donated. amines are this.

e.g. ammonia

A

Lewis base

46
Q

basic conditions convert amide to carboxylic acid salt and amine

A

basic hydrolysis of amide

47
Q

common name for 4 C chain amide

A

butyramide

48
Q

amine salts physical properties

A

odorless

very high boiling point

water soluble

aqueous (dissolve in water)

49
Q

amine solubility

A

•form Hydrogen-bonds with water

-amines of less than 6 C are water soluble

51
Q

amino group

A

amine substituent

52
Q

acidic conditions convert amide to carboxylic acid and amine salt

A

acidic hydrolysis of amide

53
Q

quaternary amines

A

choline and acetylcholine

amine salt where all 4 R groups attached to N are hydrocarbon groups

54
Q

•form strong Hydrogen-bonds with water

  • 1° amides can form 4 Hydrogen-bonds with water
  • water-soluble
A

amides solubility

55
Q

valeramide

A

common name for 5 C chain amide

56
Q

hydrolysis of amides

A

requires strong base, acid, or catalyst and heat

results in carboxylic acid and amine (or ammonia for primary amide)

57
Q

amine salts

(ammonium salts)

A

Amines react with acids to produce these

e.g. CH3-NH3+ Cl-

58
Q

requires strong base, acid, or catalyst and heat

results in carboxylic acid and amine (or ammonia for primary amide)

A

hydrolysis of amides

59
Q

•form Hydrogen-bonds with water

-amines of less than 6 C are water soluble

A

amine solubility

60
Q

amine

A

organic derivative of ammonia NH3 where one or more alkyl, cycloalkyl or aryl groups have replaced ammonia hydrogen atoms

sp3 trigonal pyramidal geometry

61
Q

basic hydrolysis of amide

A

basic conditions convert amide to carboxylic acid salt and amine

62
Q

Adenine, Guanine

Thymine, Cytosine, Uracil

types of heterocyclic rings

A

Amine bases in DNA and RNA

63
Q

odorless

very high boiling point

water soluble

aqueous (dissolve in water)

A

amine salts physical properties

64
Q

choline and acetylcholine

amine salt where all 4 R groups attached to N are hydrocarbon groups

A

quaternary amines