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Last updated 9:15 PM on 10/5/26

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22 Terms

1

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ketone/aldehyde + grignard/organLi reagents

(R-MgBr) (R-Li)

alcohol

<p>alcohol</p>

2

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aldehydes + KCN/H2O

cyanohydrins (alcohol and C-=-N groups)

<p>cyanohydrins (alcohol and C-=-N groups)</p>

3

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wittig rxn: aldehyde/ketone + PPh3

generates alkenes (forms NEW C=C bonds)

<p>generates alkenes (forms NEW C=C bonds)</p>

4

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alternate reaction to wittig reaction → horner wadsworth rxns: ketone/aldehyde + P(OMe)3

this is because the wittig reaction produces an annoying byproduct so to get around this we react with a different reaction instead

<p>this is because the wittig reaction produces an annoying byproduct so to get around this we react with a different reaction instead</p>

5

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aldehyde/ketone + H2O

diol.

mechanism will vary based on acid/base catalyst

<p>diol.</p><p>mechanism will vary based on acid/base catalyst</p>

6

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aldehyde/ketone + oxygen nucleophies (+R’’OH)

hemiacetals or acetals

PADPEAD

<p>hemiacetals or acetals</p><p>PADPEAD</p>

7

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aldehyde/ketone + nitrogen nucleophiles (ammonia, 1 amines, 2 amines)

w/ ammonia or 1 amine → imine (R—C=N-R’)

2 amine → emine

<p>w/ ammonia or 1 amine → imine (R—C=N-R’)</p><p>2 amine → emine </p>

8

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aldehyde/ketone + NaBH4

reduction to alcohol

<p>reduction to alcohol</p>

9

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aldehyde/ketone + LiAlH4

reduction like NaBH4 but it is much more reactives.

can also reduce carboxylic acid and its derivatives*

<p>reduction like NaBH4 but it is much more reactives.</p><p>can also reduce carboxylic acid and its derivatives*</p>

10

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aldehyde/ketone reductions + H2/cats

Rh

vs. Pt, Pd, Ni

<p>Rh</p><p>vs. Pt, Pd, Ni</p>

11

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COOH preparations with alcohols (3 ways)

knowt flashcard image

12

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COOH + LiAlH4

reduction to alcohol

so like just imagine it with a cooh

EXCEPT INSTEAD OF REPLACING THE C=O WITH C-OH LIKE IT DOES W KET/ALD IT GETS RID OF C=O ENTIRELY YKWIM

<p>reduction to alcohol</p><p>so like just imagine it with a cooh</p><p>EXCEPT INSTEAD OF REPLACING THE C=O WITH C-OH LIKE IT DOES W KET/ALD IT GETS RID OF C=O ENTIRELY YKWIM</p>

13

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COOH + R-OH

esterification

PADPED mechanism

<p>esterification</p><p>PADPED mechanism</p>

14

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COOH + CH2N2

methyl esters

15

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COOH to acid chlorides

SOCl2 (no pyridine)

16

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Acid Chloride Substitutions

knowt flashcard image

17

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Decarboxylation (COOH)

minus CO2

high heat

vs warming

<p>minus CO2</p><p>high heat</p><p>vs warming</p>

18

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anhydrides + H2O

if using an acid catalyst: PADPED

<p>if using an acid catalyst: PADPED </p>

19

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acid catalyzing an ester + h2o

reverse fischer esterifications (PADPED)

<p>reverse fischer esterifications (PADPED)</p>

20

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ketal, acetal, hemiacteal, hemiketal

knowt flashcard image

21

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deoxygenation of ket/ald to…

clemmsons (acidic): Zn(Hg)/HCl
wolff kishner (basic): N2H4/ heat + KOH

ket/ald to alkanes

<p>clemmsons (acidic): Zn(Hg)/HCl<br>wolff kishner (basic): N2H4/ heat + KOH<br><br>ket/ald to alkanes</p>

22

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a-halogenation of alds/kets

X2/CH3CO2H → one X attached to alpha hydrogens

X2/ NaOH → multiple X attached to alpha hydrogens

<p>X2/CH3CO2H → one X attached to alpha hydrogens</p><p>X2/ NaOH → multiple X attached to alpha hydrogens</p>