Organic Chem Exam 3 Reactions

Ketone → two alcohols coming off of the ketone carbon

[H+], H2O

Ketone → two OR groups coming off of the ketone carbon

ROH, -H2O

Ketone → ketone splits into two oxygens and are connected through a varying number (usually two) carbons

[H+], OH / \ / OH, -H2O

Ketone → ketone splits into two sulfers and are connected through a varying number (usually two) carbons

[H+], S / \ / S, -H2O

…………..N —- R

…………..||

ketone → / \

H+, RNH2, -H2O

……R —- N —- R

…………..|

ketone → / \\

H+, R2NH, H2O

………..……….N —- OH

…………….…..||

ketone → / \

H+, NH2OH, -H2O

…………..N —- NH2

…………..||

ketone → / \

H+, NH2NH2, -H2O

………….OH

…………...|

ketone → / \

1. LiAlH4

2. H3O+

…………...OH

……………|

ketone → / | \ R

1. RMgBr

2. H3O+

………….OH

……………|

ketone → / | \ CN

KCN, HCl

…………..||

ketone → / \

H2C=PPh3

……..…………..O

……...…………..||

ketone → / \ O /

RCO3H

ketone splits into two sulfers and are connected through a varying number (usually two) carbons →

H H

.\ /

./ \

Raney Ni

R / \ Br → R / \ / OH

…………….………….||

…………….………….O

1. NaCN

2. H3O+, heat

…………..………...O

………………………||

R — Br → R / \ OH

1. Mg

2. CO2

3. H3O

O ….O

.|| → ||

/ \ Cl / \OH

SOCl2

O …….O

.|| …→ ||

/ \ OH.. / \Cl

H2O

O……. O

.|| ….→ ||

/ \ Cl …./ \ OR

ROH, Pyridine

O ….O

.|| → ||

/ \ Cl / \ NH2

xs NH3

.O .………O…….…R

..|| …→… ||.….. /

/ \ Cl ……/ \ N — H

xs RNH2

O .………O……R

.|| …→… ||.….. /

/ \ Cl ……/ \ N — R

xs R2NH

O .…….OH…...H

.|| …→… .|.… /

/ \ Cl ……/ \ — H

1. xs LiAlH4

2. H3O+

O .………O

.|| …→… ||

/ \ Cl ……/ \ R

R2 CuLi

Grignard XMg—-R + Aldehyde/ketone

NaP

LiAlH4 + Aldehyde/ketone

NaP

NaBH4 + Aldehyde/ketone

NaP

Bulky hydride + Aldehydeketone

NR

M+

C triple bond —- R + Aldehyde/ketone

NaP

M (+) CN (-) + aldehyde/ketone

NaP

M (+) OH (-) + aldehyde/ketone

NaP

amines NH3 + aldehyde/ketone

NyPD PLeaD

Alcohol HOR/H(+) + Aldehyde/ketone

PaNDa PLaNDa

H2O/H(+) + aldehyde/ketone

PaNDa

Alcohol HOR/H(+) + Ester

PaNDa PLaD

H2O/H(+) + Ester

PaNDa PLaD

Alcohol HOR/H(+) + Carboxylic Acid

PaNDa PLaD

Ketone

…..O

…...||

…./….\

.R……..R

…..O

…...||

…./….\

.R……..H

Aldehyde

…..O

…...||

…./….\

.R……..O—R

Ester