Unit 6 (Lesson 34 - 39)

Question 1

amines react as () with moderate and strong acids

Answer 1

bases

Question 2

amine: acid/base reactivity trends

Answer 2

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

Question 3

factors that affect base strength of amine

Answer 3

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

Question 4

what do you look for first

Answer 4

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

Question 5

nitriles can reduce with () to form ()

Answer 5

LIALH4, H3O+ or H2 Pd/C
primary amine

Question 6

nitro groups can reduce with () to form ()

Answer 6

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

Question 7

can catalytic hydrogen reduce both imines and enamine

Answer 7

yes

Question 8

amides can be reduced with () to form ()

Answer 8

LiAlH4
amines

Question 9

neutral amines are ()

Answer 9

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

Question 10

amines can deprotonate carboxylic acids

Answer 10

irreversibly

Question 11

amines can deprotonate strong acids

Answer 11

Irreversibly

Question 12

electron donation

Answer 12

increases amine basicity

Question 13

electron withdraw

Answer 13

decreases amine basicity

Question 14

the stronger the inductive atom/group, (EWD)

Answer 14

the more weakly basic the nitrogen atom

Question 15

localized lone pair on nitrogen

Answer 15

• more readily shared
• more basic

Question 16

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

Answer 16

true

Question 17

amino acids

Answer 17

the monomeric units that make up polyamides or proteins

Question 18

pka = pH (amino acids)

Answer 18

were half the species is protonated and half is deportonated

Question 19

isoelectric point

Answer 19

is pH where overall charge = 0

Question 20

all amino acids are chiral

Answer 20

except for glycine

Question 21

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

Answer 21

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

Question 22

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

Answer 22

cysteine

Question 23

from Henderson-Hasselbalch: when pH=pKa

Answer 23

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

Question 24

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

Answer 24

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

Question 25

aliphatic

Answer 25

not aromatic

Question 26

if pH < pKa

Answer 26

protonated

Question 27

if pH > pKa

Answer 27

deprotonated

Question 28

what is an amino acid

Answer 28

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

Question 29

at physiological pH (7.3-7.4)

Answer 29

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

Question 30

D-Amino Acids

Answer 30

R configuration at the alpha carbon

Question 31

L-Amino Acids

Answer 31

S configuration at the alpha carbon

Question 32

priority for amino acid

Answer 32

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

Question 33

carbohydrates

Answer 33

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

Question 34

D-glucose fisher projection

Answer 34

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

Question 35

monosaccharides

Answer 35

simple sugars which cannot be broken down by hydrolysis - glucose

Question 36

disaccharides

Answer 36

dimers of monosacharides - cellobiose

Question 37

oligosaccharides

Answer 37

contain 3 to 8 monosaccharides - raffinose

Question 38

polysaccharides

Answer 38

contain > 8 monosaccharides - cellulose

Question 39

top of fisher projection

Answer 39

most oxidized carbon

Question 40

horizontal right

Answer 40

- always wedge - down on conformer

Question 41

horizontal left

Answer 41

- always wedge - up on conformer

Question 42

fisher projections can be rotated:

Answer 42

180 degrees but not 90 degrees

Question 43

rotation of 90 degrees

Answer 43

creates the enantiomer

Question 44

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

Answer 44

use R and S

Question 45

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

Answer 45

6, aldehyde

Question 46

the ending ose

Answer 46

indicates a carbohydrate

Question 47

an aldose

Answer 47

contains an aldehyde

Question 48

a ketose

Answer 48

contains a ketone

Question 49

L configurations are

Answer 49

naturally occuring in amino acids

Question 50

R configurations are

Answer 50

naturally occurring in sugars

Question 51

enantiomers

Answer 51

every center changes

Question 52

when multiple stereocenters are present,

Answer 52

D or L refers only to the second to last carbon

Question 53

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

Answer 53

D

Question 54

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

Answer 54

L

Question 55

aldotetroses

Answer 55

2 asymmetric carbons 2^2 = 4 stereoisomers 4 carbons

Question 56

aldopentoses

Answer 56

3 asymmetric carbons 2^3 = 8 stereoisomers 5 carbons

Question 57

aldohexoses

Answer 57

4 asymmetrical carbons 2^4 = 16 stereoisomers 6 carbons

Question 58

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

Answer 58

it undergoes rearrangement