Exam 2 Flashcards

1
Q

Aldehyde

A

R’ is H

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2
Q

Carboxylic acid

A

R’ is OH

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3
Q

Amide

A

R’ is amine (N with something)

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4
Q

Ketone

A

R’ is R’

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5
Q

Ester

A

R’ is OR’

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6
Q

Oxidation

A

Gaining bonds to O or another EN group

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7
Q

Reduction

A

Losing bonds to O or another EN group

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8
Q

LiAlH4 (LAH)

A

Strong reducer, reduces everything to 1° alcohols

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9
Q

NaBH4

A

Weak reducer, reduces ketones and aldehydes only to 1° alcohols

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10
Q

DIBAL-H

A

A reducing agent for esters and nitriles that will create an aldehyde

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11
Q

LiAlH(OtBu)3

A

A reducing agent for acid chlorides that will create an aldehyde

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12
Q

K2CrO4, H3O+

A

Strong oxidizer, uses -OR substitution with -OH as an intermediate

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13
Q

KMnO4, NaOH

A

Strong oxidizer, MnO4- and deprotonated alcohol gives the intermediate

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14
Q

Strong oxidizers

A

Take aldehydes to carboxylic acids

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15
Q

Weak oxidizers

A

1° alcohols to aldehydes or 2° alcohols to ketones

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16
Q

PCC (Cl-CrO3-)

A

Weak oxidizer, Cl-CrO3- attaches to alcohol O as LG

17
Q

Swern oxidation

  1. OS(CH3)2, (COCl)2
  2. NEt3
A

Weak oxidation, reactions stop at the aldehyde and don’t go to carboxylic acid

18
Q

DMP

A

Weak oxidation, reaction stops at the aldehyde

19
Q

Baeyer-Villiger Oxidation

A

mCPBA, creates an ester and a carboxylic acid

20
Q

Thioacetals

A

Reaction of aldehydes/ketones with thiols/thioacetals

21
Q

Thiols

A

Contains S (like EtSH, or HS–SH)

22
Q

Raney Ni, H

A

Used in ‘desulfurization’ after thioacetal formation to form a carbonyl/CH2

23
Q

Primary amines + ketone/aldehyde, acid

A

Formation of imines

24
Q

Secondary amines + ketone/aldehyde, acid cat

A

Formation of enamines

25
Q

HCN

A

Weak/slow formation of cyanohydrin with ketone/aldehyde

26
Q

NaCN, KCN

A

Strong formation of cyanohydrin with ketone/aldehyde

27
Q

Et2O, R-X and Mg/Li

A

Formation of organometallics, Mg will form RMgX (Grignard reagent) and Li forms LiX and RLi

28
Q

Grignard reagents + epoxides

A

Formation of 2° alcohols with aldehydes and 3° alcohols with ketones

29
Q

TBSCl, ImH, DmF and then TBAF

A

TBSCL protects -OH groups so Grignard reagents can add, then removed by TBAF to leave the OH

30
Q

Phosphorus ylide and aldehyde/ketone

A

Wittig reaction - forms an alkene (Z isomer only)

31
Q

Phosphonate ester and aldehyde/ketone

A

HWE reaction - forms an alkene (E isomer only)

32
Q

E isomer

A

Entgegen form - higher atomic priority on opposite sides of a double bond

33
Q

Z isomer

A

Zusammen form - higher atomic priority on the same side of a double bond