Unit 6 (Lesson 34 - 39) Flashcards

1
Q

amines react as () with moderate and strong acids

A

bases

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2
Q

amine: acid/base reactivity trends

A
  • EDG that donate via resonance increase basicity
  • alkyl groups that donate electrons increase basicity
  • sp3>sp2>sp for basicity
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3
Q

factors that affect base strength of amine

A

resonance
induction (pulling away) /hyperconjugation (donating)
hybridization (electronegativity)

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4
Q

what do you look for first

A

resonance – electron donating groups increase basicity - more so than alkyl groups

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5
Q

nitriles can reduce with () to form ()

A

LIALH4, H3O+ or H2 Pd/C
primary amine

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6
Q

nitro groups can reduce with () to form ()

A

H2 Pd/C or Zn HCl (aq)
aryl amine

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7
Q

can catalytic hydrogen reduce both imines and enamine

A

yes

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8
Q

amides can be reduced with () to form ()

A

LiAlH4
amines

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9
Q

neutral amines are ()

A
  • weak bases
  • they can use their nitrogen to accept a proton, becoming a protonated series
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10
Q

amines can deprotonate carboxylic acids

A

irreversibly

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11
Q

amines can deprotonate strong acids

A

Irreversibly

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12
Q

electron donation

A

increases amine basicity

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13
Q

electron withdraw

A

decreases amine basicity

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14
Q

the stronger the inductive atom/group, (EWD)

A

the more weakly basic the nitrogen atom

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15
Q

localized lone pair on nitrogen

A
  • more readily shared
  • more basic
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16
Q

true/false: alkyl amines are more basic than amide nitrogens

A

true

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17
Q

amino acids

A

the monomeric units that make up polyamides or proteins

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18
Q

pka = pH (amino acids)

A

were half the species is protonated and half is deportonated

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19
Q

isoelectric point

A

is pH where overall charge = 0

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20
Q

all amino acids are chiral

A

except for glycine

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21
Q

what interactions drive the folding of peptides into their tertiary, and then quaternary structures

A

H-bonds
hydrophobic interactions
-S-S-
electrostatic interactions

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22
Q

() is the only L-amino acid with an R configuration

A

cysteine

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23
Q

from Henderson-Hasselbalch: when pH=pKa

A

50% in acidic and 50% in basic form –> draw 2 species

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24
Q

when the side chains are not ionizable, the PI is ()

A

the average of the pKa’s of the carboxylic acid and the amine

25
Q

aliphatic

A

not aromatic

26
Q

if pH < pKa

A

protonated

27
Q

if pH > pKa

A

deprotonated

28
Q

what is an amino acid

A

a carboxylic acid possessing a protonated amino group at is alpha carbon

29
Q

at physiological pH (7.3-7.4)

A

amino acids exist as zwitter ions (possesing both positive and negative charges)

30
Q

D-Amino Acids

A

R configuration at the alpha carbon

31
Q

L-Amino Acids

A

S configuration at the alpha carbon

32
Q

priority for amino acid

A

1 - amino group
2 - carboxyl group
3 - R group (side chain)
4 - hydrogen

33
Q

carbohydrates

A

naturally occuring compounds with C, H, O: often with the empirical formula CH2O and a molecular formula of (CH2O)n

34
Q

D-glucose fisher projection

A

4 bars
3rd carbon (2nd bar)s is OH-H (rest of bars are (H-OH)

35
Q

monosaccharides

A

simple sugars which cannot be broken down by hydrolysis
- glucose

36
Q

disaccharides

A

dimers of monosacharides
- cellobiose

37
Q

oligosaccharides

A

contain 3 to 8 monosaccharides
- raffinose

38
Q

polysaccharides

A

contain > 8 monosaccharides
- cellulose

39
Q

top of fisher projection

A

most oxidized carbon

40
Q

horizontal right

A
  • always wedge
  • down on conformer
41
Q

horizontal left

A
  • always wedge
  • up on conformer
42
Q

fisher projections can be rotated:

A

180 degrees but not 90 degrees

43
Q

rotation of 90 degrees

A

creates the enantiomer

44
Q

when asked about what structures have the same configuration what do you do

A

use R and S

45
Q

an aldohexose is a sugar containing () carbons and an ()

A

6, aldehyde

46
Q

the ending ose

A

indicates a carbohydrate

47
Q

an aldose

A

contains an aldehyde

48
Q

a ketose

A

contains a ketone

49
Q

L configurations are

A

naturally occuring in amino acids

50
Q

R configurations are

A

naturally occurring in sugars

51
Q

enantiomers

A

every center changes

52
Q

when multiple stereocenters are present,

A

D or L refers only to the second to last carbon

53
Q

carbohydrates with a hydroxyl to the right on the last C in the fischer projection are

A

D

54
Q

carbohydrates with a hydroxyl to the left on the last C in the Fischer projection are

A

L

55
Q

aldotetroses

A

2 asymmetric carbons
2^2 = 4 stereoisomers
4 carbons

56
Q

aldopentoses

A

3 asymmetric carbons
2^3 = 8 stereoisomers
5 carbons

57
Q

aldohexoses

A

4 asymmetrical carbons
2^4 = 16 stereoisomers
6 carbons

58
Q

when D-ribose is added to an aqueous NaOH solution,

A

it undergoes rearrangement