Brainscape's Knowledge GenomeTM


Top Flashcards (Certified)
All Flashcards

OCHEM 2 > Reagents sem 2 > Flashcards

Reagents sem 2 Flashcards

(47 cards)

Start Studying
1
Q

Diene + Dienophile

A

Diels alder (forming 6 membered ring)
- Diene needs EDG
- dienophile needs EWG
- retention of OG stereochem
- ENDO rule

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

Benzene + [HNO3, H2SO4]

A

Adds NO2 via Electrophilic Aromatic Substitution

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

nitrobenzyl + [Zn, HCl]

A

nitro to amine
- can be Zn, Sn, or Fe

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

Benzene + [Br2, FeBr3]

A

adds bromine to the aromatic ring
- rds is step 1, A–>NA

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

Benzene + [Cl2, AlCl3 or FeCl3]

A

adds chlorine to the aromatic ring
- rds is step 1, A–>NA

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

Benzene + [I2, HNO3]

A

adds iodine to the aromatic ring

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

Benzene + [SO3, H2SO4]

A

adds SO3H to aromatic ring

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

Benzene with SO3H + [H2SO4, H2O, heat]

A

Takes off SO3H

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

Benzene + [alkyl halide, AlCl3 or FeBr3]

A

Friedel craft alkylation
- doesnt work on ar compounds containing an EWG
- C+ rearr can occur on halide
- Multiple alkylations may occur

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

Benzene + [1)acid chloride, AlCl3 or FeBr3, 2)H2O]

A

Friedel craft acylation
-doesnt work on ar compounds containing an EWG
- no rearr
- no multiple acylatinos
- H2O is needed

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

What does the clemmenson reduction do and what are the reagents?

A

Zn(Hg), HCl
- reduces C=O

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

Anisole + [CO, HCl, AlCl3/CuCl]

A

Gatterman Koch synthesis
- adds aldehyde para on
- doesnt have to have anisole, can be any aromatic compund

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

Explain nucleophilic aromatic substitution (NAS): Addition Elimination

A

Substitutes nuc with LG
- requires EWG in o or p position to LG
- can work with NH3, NaOH, or NaOR

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

Explain nucleophilic aromatic substitution (NAS): elimination addition

A
  • Creates benzyne
  • Works with strong base (NaNH2 or NaNr2) or base with heat (NaOH, NaOR)
  • attacks both benzyne spots equally
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

Explain the reaction of carboxylic acid with [1)2 eq of grignard 2)H3O+]

A

turns it into a ketone
- first grignard does acid base
- second grignard attacks carbonyl

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

explain the reaction of nitrile with [1) grignard 2)H3O+]

A

turns it into imine then ketone via hydrolysis

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

explain the reaction of nitrile with [1) DIBAL-H 2)H3O+]

A

Turns nitrile into aldehyde
- only 1 H-
- hydrolysis turns it from “imine” to aldehyde

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
18
Q

CA + [1)SOCl2 2)LiAlH(OtBu)3]

A

1) SOCl2 turns it into acid chloride
2) turns it into aldehyde
- must be 2 steps

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

Acid Chloride + [R2CuLi]

Study These Flashcards
A

turns it into ketone

20
Q

Ester + [1)DIBAL-H 2)H2O]

Study These Flashcards
A

turns ester into aldehyde

21
Q

Ketone + [1°,2° Amine + acid]
- what would happen if reacted with a 3° amine

Study These Flashcards
A

forms imine
- 3° amine would form an enamine
- reversible reaction

22
Q

Ketone/aldehdye + [2eq of ROH + Acid]

Study These Flashcards
A

formation of acetal
- reversible reaction
- remember aldehyde is faster than ketone

23
Q

Explain what happens when Ph3P reacts with [1) Ch3Ch2Br 2) BuLi 3) Acetone]

Study These Flashcards
A
  • steps 1 and 2 with the starting material create the wittig reagent
  • reaction with acetone replaces O on carbonyl with Carbon chain (Z)
24
Q

Aldehydes + [Ag2O]

Study These Flashcards
A

turns it into CA

25
Aldehyde/Ketone with [**1)NH2NH2, pH~4.5 2)KOH, heat**]
Wolff-Kishner reagents - removes carbonyl - Use when dealing with amides, keep acetals, keep nitros
26
Explain the reaction that takes place when an amine reacts with either an acid chloride + pyridine or acid anhydride
Nucleophilic Acyl Substitution rxn that forms amide - reversible reaction (can be hydrolyzed) - pyridine is there to neutralize HCl formed when reacted with acid chloride
27
Explain the reaction that takes place when a 1° amine on carbon chain reacts with [**1)CH3I excess 2)Ag2O, H2O**]
Hoffman elimination 1) creates 4° ammonium salt 2) creates -OH that does E2 and creates hoffman product - ammonium salt LG and H need to be ANTI
28
Explain the reaction that takes place when an amine on carbon chain reacts with [**H2O2, heat**]
Cope oxidation - forms 3° amine oxide - oxide used to do intramolecular E2 - syn elimination and forms hoffman product
29
Aniline + [**NaNO2 HCl**]
forms diazonium salt from the amine group (NH2) - whole chart of various nucleophiles that can be used with diazonium
30
Describe the reaction of alkyl halide with activated Pthalamide
Gabriel synthesis - creates 1° amine via SN2
31
Describe the reaction of alkyl halide with [**1)Azide (N3-) or Cyanide (-CN) 2)LiAlH4 3) H2O**]
Creates 1° amine via SN2 - using NaN3 or NaCN
32
CA + Amine
forms amide - reversible reaction - first step forms carboxylate and ammonium salt
33
CA with CH2N2
forms methyl ester - irreversible - DF is N2+ leaving as a gas
34
CA + [**1)BH3, THF 2)H3O+**]
selectively reduces CA into 1° alcohol - does not react with ketone or aldehyde - BH3, THF can also be seend as B2H6
35
Describe the hydrolysis of nitriles (CN) in harsh and mild conditions
mild condition: rt - forms amide harsh conditions: Heat or reflux - forms CA CAN BE ACIDIC OR BASIC HYDROLYSIS
36
Amide + [**1)LiAlH4 2)H2O**]
reduces the carbonyl of the amide, turning it into an amine
37
Dicarboxylic acid + acid chloride + heat = _______
cyclic anhydride - only possible for 5-6-membered rings - via condensation rxn
38
Lactones are formed via _______ while Lactams are formed via _______
fischer esterification (condensation) condensation reaction of amine and CA
39
1° Amide + [**POCl3 or P2O5, or SOCl2**]
turns 1° amide into nitrile
40
Enol + [**Br2, CH3COH**]
acidic alpha halogenation - adds halogen to alpha C - up to 2 halogenations but gets slower everytime
41
Enolate + [**Br2, KOH, H2O**]
basic alpha halogenation - adds as many halogens as possible - if methyl ketone and excess halogen, then haloform reaction leads to carboxylate
42
CA + [**1)Br2/PBr3 2)H2O**]
HVZ reaction - 1) adds Br to alpha position and substitutes OH - 2) turns acid bromide into CA
43
Explain the aldol condensation rxn
mod base (-OH) deprotonates small amount of ald or ketone and then they are combined forming an "aldol" - if heat is added then dehydration occurs and the alpha,beta-unsaturated carbonyl is formed
44
Explain the claisen ester condensation rxn
mod base (-OR) deprotonates small amount of ester and then they are combined forming an "beta-dicarbonyl system" - reagents 1) NaOR 2) H3O+ - H3O+ needed to reprotonate alpha carbon
45
Dicarbonyl ester + [**H3O+ heat**]
malonic ester (decarboxylation rxn) - makes substituted derivative of acetic acid - driven by CO2 (g) leaving - cyclic transition state - acetoacidic is when one side is ketone not ester
46
α,β-unsaturated carbonyl + [weak nuc]
micheal rxn - adds 1,4 - weak nucs include -CN, R2CuLi, enamine, enolate, amine, dicarbonyl system
47
What is robinson annulation?
- a micheal rxn followed by aldol condensation - makes fused 6 member ring in one step

OCHEM 2 (13 decks)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2025 Bold Learning Solutions. Terms and Conditions