Orgo 2 Exam 2

0.0(0)
studied byStudied by 0 people
learnLearn
examPractice Test
spaced repetitionSpaced Repetition
heart puzzleMatch
flashcardsFlashcards
Card Sorting

1/153

encourage image

There's no tags or description

Looks like no tags are added yet.

Study Analytics
Name
Mastery
Learn
Test
Matching
Spaced

No study sessions yet.

154 Terms

1
New cards

friedel-craffs alkylation

limitations

  1. any alkyl halide can be used (single bonds only)

  2. impossible to stop at mono-alkylation (multiple substitutions)

  3. wont react if theres a strong deactivator

<p>limitations</p><ol><li><p>any alkyl halide can be used (single bonds only)</p></li><li><p>impossible to stop at mono-alkylation (multiple substitutions)</p></li><li><p>wont react if theres a strong deactivator</p></li></ol><p></p>
2
New cards

friedel-acylation

knowt flashcard image
3
New cards

reduction

knowt flashcard image
4
New cards

diazonium

knowt flashcard image
5
New cards

aromatic rxns

knowt flashcard image
6
New cards

activating groups


faster rxn, lone pair e- directly connected to benzene, neg or partial neg charge

ortho/para director

<p><br>faster rxn, lone pair e- directly connected to benzene, neg or partial neg charge</p><p>ortho/para director</p>
7
New cards

deactivating groups

slower rxn, pos or partiall pos charge

meta director

exception: halogens ortho/para deactivators

<p>slower rxn, pos or partiall pos charge</p><p>meta director</p><p>exception: halogens ortho/para deactivators</p>
8
New cards

NAS

<p></p>
9
New cards

3-chloro-4-cyclohexylbutanone

IUPAC

<p>IUPAC</p>
10
New cards

2-ethyl-6-isopropoxy-5-oxocental

IUPAC

<p>IUPAC</p>
11
New cards

nona-4,8-diene-2,7-dione

IUPAC

<p>IUPAC</p>
12
New cards

5-oxohexanedial

IUPAC

<p>IUPAC</p>
13
New cards

aldehydes


when naming these,

-al on end

highest priority in naming

14
New cards

ketones

when naming these,

-one on end

-oxo internal

15
New cards

cyclopentanecarbaldehyde

knowt flashcard image
16
New cards

formaldehyde

knowt flashcard image
17
New cards

acetaldehyde

knowt flashcard image
18
New cards

acrolein

knowt flashcard image
19
New cards

crotonaldehyde

knowt flashcard image
20
New cards

acetone

knowt flashcard image
21
New cards

reduction

knowt flashcard image
22
New cards

reduction

knowt flashcard image
23
New cards

poisoned pd

knowt flashcard image
24
New cards

gutterman ruch

knowt flashcard image
25
New cards

ozone cleavage

knowt flashcard image
26
New cards

silver mirror test

knowt flashcard image
27
New cards

nucleophilic addition rxn

knowt flashcard image
28
New cards

aldehydes


more reactive than ketones for two reasons:

sterics: h smaller group, more room for nucleophile to attack

electronics: alkyl gets past e- density easier, less electrophilic, attracts nucleophile more readily

29
New cards

acids

when naming these,

methane → methanoic acid

on chain names, drop the ending e and replace with -oic acid

30
New cards

heptanedioic acid

IUPAC

31
New cards

7-chlorooctanoic acid

IUPAC

<p>IUPAC</p>
32
New cards

nitrile

when naming these,

add nitrile at the end of the chain name

ethane → ethanenitrile

33
New cards

properties of carboxylic acids

  1. dimerize, high boiling point

  2. acidic

  3. pka usuallly from 4-5 when in the body

34
New cards

right

more acidic?

<p>more acidic?</p>
35
New cards

right

more acidic?

<p>more acidic?</p>
36
New cards

right

more acidic?

<p>more acidic?</p>
37
New cards

right

more acidic?

<p>more acidic?</p>
38
New cards

right

more acidic?

<p>more acidic?</p>
39
New cards

CN, hydrolysis

prep of carb acids

<p>prep of carb acids</p>
40
New cards

Na2CrO7, LAH

prep of carb acids

<p>prep of carb acids</p>
41
New cards

cleavage (KMnO4, acid/neutral)

prep of carb acids

<p>prep of carb acids</p>
42
New cards

cleavage (KMnO4 or O3)

prep of carb acids

<p>prep of carb acids</p>
43
New cards

KMnO4

prep of carb acids

<p>prep of carb acids</p>
44
New cards

CO2, H3O

prep of carb acids, grignard

<p>prep of carb acids, grignard</p>
45
New cards
<p>KCN</p>

KCN

prep of nitrilles

46
New cards

SOCl2

prep of nitriles

degradation of a primary amide

47
New cards

LAH, H2O

carb acid rxn

<p>carb acid rxn</p>
48
New cards

BH3, THF

carb acid rxn

<p>carb acid rxn</p>
49
New cards

BH3, THF

carb acid rxn

<p>carb acid rxn</p>
50
New cards

NAH, iodopropyl OR propanol, H3O

carb acid rxn

fischer tropsch esterification

<p>carb acid rxn</p><p>fischer tropsch esterification</p>
51
New cards

acid/base with heat

nitrile rxn

<p>nitrile rxn</p>
52
New cards

LAH, H3O

nitrile rxn

nitrile to primary amine

<p>nitrile rxn</p><p>nitrile to primary amine</p>
53
New cards

RMgX, H3O

nitrile rxn

grignard

<p>nitrile rxn</p><p>grignard</p>
54
New cards

acid halides

when naming these:

formic acid → formyl chloride

propionic acid → propionyl acid

ending ic swap to yl

55
New cards
56
New cards

benzoyl bromide

IUPAC

<p>IUPAC</p>
57
New cards

esters

when naming these:

name the substituent not attached to the carbonyl first, then the parent chain

ethane → ethanoate

replace e with -oate

58
New cards

isopropylpentanoate

IUPAC

<p>IUPAC</p>
59
New cards

ethylethanoate (ethylacetate)

IUPAC

<p>IUPAC</p>
60
New cards

t-butylcyclohexane carboxylate

IUPAC

<p>IUPAC</p>
61
New cards

amides

when naming these:

ethane → ethanamide

replace e with -amide

use N- to indicate groups attached

62
New cards

ethanamide (acetamide)

IUPAC

<p>IUPAC</p>
63
New cards

N-methylacetamide

IUPAC

<p>IUPAC</p>
64
New cards

N,N-dimethylacetamide

IUPAC

<p>IUPAC</p>
65
New cards

N-isopropylbutanamide

IUPAC

<p>IUPAC</p>
66
New cards

N-ethyl-N-methylacetamide

IUPAC

<p>IUPAC</p>
67
New cards

thioesters

when naming these:

name the substituent not attached to the carbonyl first, then the parent chain

ethane → ethanoate

replace e with -oate

then, add thio- in front of the parent chain

68
New cards

ethylthiobutanoate (ethylbutanethioate)

IUPAC

<p>IUPAC</p>
69
New cards

methylcyclopentanecarbothioate

IUPAC

<p>IUPAC</p>
70
New cards

acid anhydride

when naming these;

name the substituents same as an acid then add anhydride at the end

benzoic acid → benzoic anhydride

71
New cards

benzoic anhydride

IUPAC

<p>IUPAC</p>
72
New cards

acetic benzoic anhydride

IUPAC

<p>IUPAC</p>
73
New cards

nucleophilic aryl substitution

knowt flashcard image
74
New cards

SOCl2/CHCl3 or PBr3

carb acid → acid halide

<p>carb acid → acid halide</p>
75
New cards

heat

carb acid → acid anhydride

<p>carb acid → acid anhydride</p>
76
New cards

NaH/iodopropane

carb acid → ester

<p>carb acid → ester</p>
77
New cards

H3O

carb acid → ester

fischer tropsch esterification

<p>carb acid → ester</p><p>fischer tropsch esterification</p>
78
New cards

R2NH

carb acid → amide

<p>carb acid → amide</p>
79
New cards

DCCI/propylamine

carb acid → amide

<p>carb acid → amide</p>
80
New cards

LAH/H2O

carb acid → alcohol

<p>carb acid → alcohol</p>
81
New cards

BH3, THF/H3O

carb acid → alcohol

<p>carb acid → alcohol</p>
82
New cards

NaOH/H2O pyr

acid halide → acid

<p>acid halide → acid</p>
83
New cards

ethanol/pyr

acid halide → ester

sterics are critical here, 1 > 2 > 3

<p>acid halide → ester</p><p>sterics are critical here, 1 &gt; 2 &gt; 3</p>
84
New cards

2 NH3

acid halide → amide

<p>acid halide → amide</p>
85
New cards

2 eq. dimethylamine

acid halide → amide

<p>acid halide → amide</p>
86
New cards

LAH/H3O

acid halide → alcohol

<p>acid halide → alcohol</p>
87
New cards

CH3MgCl/H3O

acid halide → alcohol

grignard

<p>acid halide → alcohol</p><p>grignard</p>
88
New cards

(CH3)2CuLi OR Li(O-tBu)3AlH

acid halide → ketone

<p>acid halide → ketone</p>
89
New cards

ethanol/NaOH

acid anhydride → ester

<p>acid anhydride → ester</p>
90
New cards

ethylamine/NaOH

acid anhydride → amide

<p>acid anhydride → amide</p>
91
New cards

H3O

acid anhydride → carb acid

92
New cards

H3O

ester → carb acid

93
New cards

NH3/ether

ester → amide

<p>ester → amide</p>
94
New cards

ester to alcohol

ways for _______________

  1. LAH

  2. DIBAH → aldehyde

  3. RMgX

95
New cards

H3O

amide → carb acid

<p>amide → carb acid</p>
96
New cards

LAH/H3O

amide → amine

<p>amide → amine</p>
97
New cards

SOCl2/pyr OR P2O5/pyr OR POCl3/pyr

amide → nitrile

<p>amide → nitrile</p>
98
New cards

2-methylpropylbutanoate

IUPAC

<p>IUPAC</p>
99
New cards

alpha carbon

bulky base vs regular base

<p>bulky base vs regular base</p>
100
New cards

alpha carbon

knowt flashcard image