Chem 238 Final

Front 1

UVA

Back 1

315-400 nm

may contribute to
1. premature aging
2. skin cancer
3. cataracts

Front 2

compounds that protects against UVA (3)

Back 2

1. avobenzone
2. TiO2
3. ZnO

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SPF

Back 3

sun protective factor

indicates amount of sun protection

SPF = (MED for skin w/ sunscreen) / (MED for skin w/o sunscreen)

only refers to protection against UVB

Front 4

MED

Back 4

minimal erythemal dose

amount of time one can stay in sun before getting burned

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safety - isopropyl alcohol

Back 5

flammable
irritant

Front 6

safety - sulfuric acid/nitric acid

Back 6

strong acid - can cause skin burns

Front 7

safety - methanol

Back 7

volatile
irritant

Front 8

safety - methyl benzoate

Back 8

volatile
irritant

Front 9

safety - methyl m-nitrobenzoate

Back 9

strong irritant

Front 10

UVB

Back 10

290-315 nm

contributes to
1. skin cancer
2. skin aging
3. delayed sunburn
4. catarcts
4. immunosuppresion

Front 11

UVC

Back 11

100-290 nm

can be lethal, but totally absorbed by ozone in earth's atmosphere

have highest energy of UV rays

Front 12

semi-empirical methods

Back 12

simplification of molecular mechanics equations

predicts results of reactions where bonds are forming/breaking

Front 13

kinetic control

Back 13

ratio of products dependent on relative energies (stabilities) of TRANSITION STATES

ex: markovnikov addition of HBr

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thermodynamic control

Back 14

ratio of products depends on relative energies (stabilities) of PRODUCTS

can be favored by higher temps or longer times

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1,2-addition of HBr to butadiene

Back 15

predominant at low temps

major product = 3-bromo-1-butene

Front 16

1,4-addition of HBr to butadiene

Back 16

predominant at high temps (under thermodynamic control)

major product = 1-bromo-2-butene

LOWER energy than 3-bromo-1-butene

Front 17

borneol

Back 17

MINOR, endo product of the borohydride reduction of camphor

formed by EXO ATTACK of hydride ion on carbonyl carbon

Front 18

isoborneol

Back 18

MAJOR, exo product of the borohydride reduction of camphor

formed by ENDO ATTACK of hydride ion on carbonyl carbon

Front 19

safety - sodium borohydride

Back 19

corrosive
irritant

Front 20

safety - camphor/isoborneol

Back 20

irritants
flammable

Front 21

organometallic compounds

Back 21

compounds containing carbon-metal bond

Front 22

organosodium/organopotassium reagents

Back 22

highly ionic

carbon acts as powerful base

pyrophoric (burst into flames upon air exposure)

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organomagnesium

Back 23

GRIGNARDS REAGENT

ionic - strong carbon nucleophile/base

covalent - soluble in many organic solvents

Front 24

ketones + RMgX --> ??

Back 24

tertiary alcohols

Front 25

aldehydes + RMgX --> ??

Back 25

secondary alcohols

Front 26

esters + 2 RMgX --> ??

Back 26

tertiary alcohols

Front 27

epoxides + RMgX --> ??

Back 27

alcohol

Front 28

carbon dioxide + RMgX --> ??

Back 28

carboxylic acid (R-COOH)

Front 29

water + RMgX --> ??

Back 29

alkane (RH)

Front 30

nitriles (CN) + RMgX --> ??

Back 30

ketones

Front 31

metalation

Back 31

terminal acetylene + RMgX --> alkanes

Front 32

diethyl ether

Back 32

ether commonly used to prepare grignard reagent

extremely volatile, flammable
low affinity for water
heavier than air - acts as barrier/prevents water from entering rxn

Front 33

THF

Back 33

tetrahydrofuran

commonly used in preparation of grignard reagent

less volatile/flammable (compared to diethyl ether)

soluble in water; readily absorbs water from atmosphere

used when higher bp ether needed

Front 34

safety - THF

Back 34

highly flammable

Front 35

2,4-DNP test

Back 35

tests for presence of aldehydes and ketones

(+) = formation of precipitate
yellow/orange --> aliphatic
orange/red --> aromatic (conjugated)

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tollen's test

Back 36

tests for presence of aldehydes

(+) = silver mirror/black precipitate formation

reaction: aldehyde + silver-ammonia complex --> silver mirror

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Schiff's test

Back 37

tests for presence of aliphatic (nonaromatic) aldehydes

(+) = instantaneous color change to wine-purple color

reagents:
1. rosaniline hydrochloride
2. sodium bisulfate

Front 38

safety - Schiff's reagent

Back 38

corrosive
irritant

Front 39

iodoform (haloform) teset

Back 39

tests for presence of methyl group attached to carbonyl carbon

(+) = yellow precipitate (iodoform-CHI3) appears

Front 40

fischer esterification

Back 40

sythesis of esters

carb acid + alcohol --(sulfuric acid) --> ester + water

Front 41

ways to drive fischer esterification to competion (2)

Back 41

excess alcohol

remove one/both of products formed

Front 42

hydrolysis of benzoyl chloride

Back 42

benzoyl chloride + water --> benzoic acid

Front 43

ammonolysis of benzoyl chloride

Back 43

benzoyl chloride + ammonia --> benzamide

Front 44

synthesis of acid chlorides

Back 44

carboxylic acids --(SOCl2)--> acid chloride

can also use oxalyl chloride

Front 45

synthesis of methyl benzoate

Back 45

benzoic acid --(cat. H2SO4/methanol)--> methyl benzoate + water

Front 46

safety - sulfuric acid

Back 46

toxic
corrosive

Front 47

safety - benzoic acid

Back 47

irritant

Front 48

safety - benzoyl chloride

Back 48

lachrymator ("tear gas")

Front 49

safety - ammonia

Back 49

corrosive
toxin

Front 50

7 basic odors

Back 50

1. peppermint
2. pungent
3. putrid
4. camphor
5. floral
6. musk
7. ether

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lactones

Back 51

cyclic esters with 6 or fewer carbons

Front 52

macrolides

Back 52

cyclic esters with more than 9 carbons

Front 53

preparation of esters

Back 53

carboxylic acids + alcohols + sulfuric acid (H2SO4)

add water, exctract organic upper layer (ester)

Front 54

safety - low MW carboxylic acids

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volatile
irritants
corrosive

Front 55

4 general types of aldehyde/ketone reactions

Back 55

1. nucleophilic addition to carbonyl carbon

2. substitution at alpha-hydrogen

3. condensation reactions

4. oxidation reactions

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aldol

Back 56

beta-hydroxycarbonyl compound

formed when alpha-carbon of one carbonyl compound bonds to carbonyl carbon of another compound

Front 57

aldol condensation

Back 57

alpha carbon of one carbonyl compound bonds to carbonyl carbon of another compound

can be acid or base catalyzed

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preparation of TPCP (tetraphenylcyclopentadienone)

Back 58

dibenzyl ketone + benzil --(cat. KOH / ethanol)--> TPCP and H20

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wavelength - 400 nm

Back 59

color of light at this wavelength = violet

resulting color = yellow

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wavelength - 430 nm

Back 60

color of light at this wavelength = blue

resulting color = orange

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wavelength - 500 nm

Back 61

color of light at this wavelength = green

resulting color = red

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wavelength -580 nm

Back 62

color of light at this wavelength = yellow

resulting color = violet

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wavelength - 600 nm

Back 63

color of light at this wavelength = orange

resulting color = blue-violet

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wavelength - 650 nm

Back 64

color of light at this wavelength = red-orange

resulting color = blue-green

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wavelength - 700 nm

Back 65

color of light at this wavelength = red

resulting color = green

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safety - KOH

Back 66

toxic
corrosive

Front 67

safety - hexanes

Back 67

flammable
volatile
irritants

Front 68

eschweiler-clarke reaction

Back 68

specific for synthesis of tertiary amines

primary amine + formaldehyde + formic acid --> tertiary amine

Front 69

preparation of N,N-dimethylbenzylamine

Back 69

benzylamine + formic acid + formaldehyde --> N,N-dimethylbenzylamine

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dragendorff's reagent

Back 70

sprayed on TLC plates in synthesis of tertiary amine lab

mixture of bismuth subnitrate and KI dissolved in acetate

used to detect amines

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safety - formic acid

Back 71

volatile, irritant

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safety - all amines

Back 72

toxic
irritants

Front 73

plastoquinone

Back 73

critical component in electron transport in photosynthesis of plants

displaced by triazine herbicides

Front 74

triazine ring

Back 74

aromatic ring with 3 N's

Front 75

preparation of simazine

Back 75

cyanuric chloride + excess ethylamine --(acetone, 0-25 C)--> simazine

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peptide bond or amide bond

Back 76

amide bond between carboxyl group of one AA and the amino group of another AA

strong; found in enzymes, protein, chitin

Front 77

carbodi-imides

Back 77

selectively couple amines and carboxylic acids --> amides

R-N=C=N-R'

Front 78

aminopeptidases

Back 78

enzymes that remove single AAs from amino or N-terminus side of chain

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carboxypeptidases

Back 79

enzymes that hydrolyze peptide bonds at free carboxylate end of AAs

Front 80

aspartame

Back 80

methyl ester dipeptide of aspartic acid and phenylalanine

Front 81

diketopiperazine (DKP)

Back 81

compound that forms when aspartame rearranges due to heat

Front 82

permanganate test or baeyer's test

Back 82

tests for presence of double bonds, primary/secondary alcohols, and aldehydes

(+) = deep purple (KMnO4) --> brown precipitate (Mn dioxide)

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ceric nitrate test

Back 83

tests for presence of alcohols (usually primary)

(+) = red/brown precipitate formed

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safety - KMnO4

Back 84

toxic
irritant

Front 85

safety - CAN

Back 85

irritant
oxidizer

Front 86

electron withdrawing groups

Back 86

meta-directors

carbonyl (C=O)
nitrile (CN)
nitro (NO2)
sulfonyl (SO2R)