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DAT > DAT Destroyer O Chem > Flashcards

DAT Destroyer O Chem Flashcards

1
Q

What is the tollens reagent

A

Ag(NH3)2

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2
Q

What does the tollens reagent Ag(NH3)2

A

they are oxidizing agents that convert aldehydes to acids

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3
Q

what is the equation for double bond equivalents

A

(2C + 2 - H - X + N) / 2

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4
Q

what reaction is caused by
PCC
——->
CH2Cl2

A

the oxidation of alcohol to an aldehyde or ketone

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5
Q

What is a grignard reagent

A

an RMgX

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6
Q

what does a grignard reagent do

A

the R group Nu attacks the Carbonyl carbon and attaches, forming an alcohol

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7
Q

What is an azeotrope

A

an azeotrope is a constant boiling mixture that is made up of substances in a certain ratio that simple distillation cannot separate

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8
Q

Where do radicals usually add

A

the most substituted carbon

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9
Q

how is conversion from glucose to fructose started

A

removal of the alpha H

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10
Q

what is a solvolysis reaction

A

when the solvent acts as a nucleophile

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11
Q

which has higher boiling points alcohols or ethers

A

alcohols

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12
Q

what is a constitutional isomer

A

same formula, different connectivity

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13
Q

what do electron withdrawing groups do to adjacent bases

A

make them less basic

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14
Q

which is more basic a lone pair in an sp3 or sp2 orbital

A

the lone pair in the sp3 orbital

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15
Q

What does ___ do
RCl
—–>
AlCl3

A

it adds the R (at least to benzene)

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16
Q

What does ____ do to a primary alkane
K2Cr2O7
————->
H3O+

A

converts it to a carboxylic acid

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17
Q

what does Br2/FeBr3 do

A

adds bromine

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18
Q

What does _____ do to benzene
HNO3
——–>
H2SO4

A

adds a nitro group

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19
Q

What are activating groups (electron donators)

A

2HN- (How nice of you to donate)

  • OH (OH, you need some money)
  • OR (OR i can give you food)
  • R (Really, I’ll give you money
  • aryl groups (Plate of food - its an aromatic group)
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20
Q

What are deactivating groups (electron withdrawers)

A 
carbonyls
SO3H (SO! I ain't giving you money)
Cyanide (CN) is CNister
NO2 (You want money, NO!)
NR3 (No really, I'm not givin you money)
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21
Q

acivators and deactivators = o,p,m directors

A

Activators are OP directors

Deactivators are M directors

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22
Q

What does _______ do
I 2 excess
————–>
Oh-

A

it’s the haloform reaction

it removes a CH3 from a methyl ketone, replacing it with an O- group

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23
Q

what is heat of combustion

A

the heat required to break down the molecule

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24
Q

What does a high heat of combustion = less stability

A

because it does

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25
Q

Which has a higher heat of combusiton, the more or less substituted alkane

A

the less

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26
Q

What is the product of the claisen condensation

A

an anhydride

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27
Q

what does the dieckmann condensation do

A

cyclizes half of a diester

28
Q

what kinds of molecules would easily be converted into a grignard reagent

A

those without acidic protons

29
Q

what is the product of a benzylacid chloride and a benzoic acid

A

an anhydride with two benzyl groups

30
Q

what does CH3CHOOOH do to alkenes

A

forms an epoxide

31
Q

what does ______ do
C2H5OH
————–>
H+

A

the C2H5O- Nu attacks the more substituted carbon

32
Q

What does ________ do
TsCl
——>
Pyr

A

the Ts replaces the H of an OH group (to be later replaced by another Nu)

33
Q

how are bicyclo compounds named

A
  1. bridghead recieves C1

2. Numbers in parentheses indicate how many carbons are between the two bridgeheads

34
Q

what things give positive tests with Br2/CCl4 and cold dilute KMnO4

A

things with double bonds (benzene doesn’t count, the double bonds are not normal due to resonance hybridization)

35
Q

how many products can the chlorination of 2 methylbutane

A

6 (including stereoisomers)

36
Q 
which things favor which type of reaction
Nucleophilic substitution
Nucleophilic addition
Electophilic addition
electrophilic substitution
A

Esters and amides do Nu substitution
Aldehydes and ketones do Nu addition
alkenes and alkynes do electrophilic addition
aromatic compounds usually do electrophilic substitution

37
Q

What does _____ do
LiAlH4, Et2O
——————->
H3O+

A
  1. reduces aldehydes to primary alcohols
  2. reduces ketones to secondary alcohols
  3. esters into primary alcohols
  4. carboxylic acids into primary alcohols
  5. doesn’t reduce double or triple bonds
38
Q

what happens when you react an aldehyde with a amide

A

the carbonyl carbon of the aldehyde double bonds to the Nitrogen of the amide

39
Q

what does K2Cr2O7/H do to a secondary alcohol

A

turns it into a ketone

40
Q

what does (R)3 P+ -CH2/ DMSO do to a carbonyl

A

replaces the O with the R group

41
Q

what does B2H2, THF / H2O2, OH- do to a double bond

A

anti markovnikov addition of OH to the double bond

42
Q

What does 1) CH3 MgBr / 2) H3O+ do with esters

A

2 moles of the grignard will react with it to form a tertiary alcohol

43
Q

what is a lactone

A

a cyclic ester

44
Q

What happens when an aldehyde is reacted with dilute acid or a base

A

if it has alpha hydrogens it will do aldol condensation

45
Q

What will Cl2(excess) /OH- do to a carbonyl

A

it will replace all of the alpha hydrogens

46
Q

When can heating carboxylic acids result in decarboxylation

A

only when you heat a beta-keto acid (a carboxylic acid on the beta carbon of a Ketone)

47
Q

what kind of reaction is a double dehydrohalogenation

A

E2

48
Q

would R-CN be replaced by I- in a reaction

A

nope

49
Q

What does a large sterically hindered base do to a carbonyl

A

it will remove the most accessable alpha H

50
Q

if you have an acid with a pKa of 5, at pH 7 is it mostly the acid or the ion

A

ion

51
Q

When do we create a carbocation

A 
nitration
sulfonation
alkylation
acylation
halogenation
52
Q

What happens when doing alkylation if you have 3 carbons or more in a linear fashion

A

it rearranges, and will bond a more substituted carbon

53
Q

what does Br2/heat do when there is a C-h group off of a benzene ring

A

it will replace the benzylic H

54
Q

what are exceptions to the rule that atoms bound to more electronegative atoms are electron withdrawing groups

A 
NO = activating group
Halogens = activating groups

Secondary and tertiary Amines are withdrawing groups even though they have less electronegative atoms after it

55
Q

what does Zn(Hg)/HCL do to a carbonyl group

A

completely remove the carbonyl, turn it into CH2

56
Q

what does 1) Sn, HCL/ 2) OH- do to a nitrobenzene

A

turns the nitro group into an amine (aniline)

57
Q

why does Br2 and light, or NBS attack benzylic H’s

A

because that creates the most stable radical

58
Q

what do peroxide initiators do

A

allow one to create a polymer

59
Q

what does Br2/CH2Cl2 do to a double bond

A

adds Br to both sides of the double bond (reduces it too)

60
Q

What is the order of best to worst leaving groups amongst the halides

A

I>Br>Cl>F

61
Q

What is 3 benzene groups attached to a P with a lone pair going to do to a alkyl halide

A

replace the halide. then it is deprotonated by a strong base (Li) this creates a witting reagent.

62
Q

What does the witting reagent do to a carbonyl

A

replaces the C=O bond with C=R(of the wittig reagent)

63
Q

what is the order of polarity

least to most

A 
alkanes
alkenes
ethers
esters
aldehydes and ketones
alcohols
carboxylic acids
64
Q

what would H3O+ do to a lactone

A

lacone is a cyclic ester

it cuts it and OH adds to the carboxylic acid

65
Q

what does the jones reagent do to alcohols

A

turns them into aldeydes and ketones

66
Q

what do electron withdrawing groups do to acidity

A

increase it

67
Q

what happens to amides when reacting with water

A

the NH group will be replaced by O- in basic conditions

the NH group will be replaced by OH in acidic conditions

DAT (14 decks)

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