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Organic Chemistry Reactions and Mechanisms, Study Guides, Projects, Research of Organic Chemistry

University of Mary Hardin-Baylor (UMHB)Organic Chemistry

A series of organic chemistry reactions and corresponding mechanisms, including predicting major products, synthesizing molecules, and explaining selectivity. Reactions involve various reagents and conditions.

Typology: Study Guides, Projects, Research

2021/2022

Uploaded on 09/27/2022

gaurish
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(1) Predict the major product from each reaction. If you expect no reaction, indicate.
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
N
H
Ac2O
pyridine
DMAP
O
OH
OH
O
O2N
PPh3, DEAD
O
NH2
CO2H
DCC
O
H
O
OCH3
CH3CH2OH
TsOH(cat.)
O
O
N
H
HOAc (cat.)
O
HCN
O
HPh3P=CHPh
O
NH
TsOH
H
N
O
O
O
O
NO2
OEt
OEt
O
OCH3
OH
CN
N
CH3CH3
N
O
O
N
HO
pf3
pf4

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( 1 ) Predict the major product from each reaction. If you expect no reaction, indicate.

(a) (b) (c) (d) (e) (f) (g) (h)

N

H

Ac 2 O pyridine

DMAP

O

OH

OH

O

O 2 N

PPh 3 , DEAD O NH 2

CO 2 H

DCC

O

H

O

OCH 3

CH 3 CH 2 OH

TsOH(cat.) O

O

N

H

HOAc (cat.)

O

HCN

O

H Ph^3 P=CHPh O NH TsOH

H

N

O

O

O

O

NO 2

OEt OEt O

OCH 3

OH

CN

N

CH 3 CH^3

N

O

O

N

H

O

( 3 ) Fill in the compounds in the following roadmap (only show the major product for each step)

1 ) O 3 then Me 2 S

2 ) HOCH 2 CH 2 OH,

TsOH, MgSO 4 (only one equivalent) 3 ) MgBr then work-up 4 ) Ac 2 O, pyridine 5 ) HCl, H 2 O 6 )^ NH^2 OH HOAc (cat.)

DMAP

O

O

H

( 2 ) Which of these two compounds is more acidic and why?

O

O 2 N OH

O

H 3 CO OH

O

O

O

O

O

Ph OH O

O

Ph O

O

O

H

Ph O

O

N

H

Ph O

O

OH

The nitro group is electron withdrawing and helps stabilize the conjugate base (carboxylate) O O 2 N O

( 9 ) List the reagents (in order) needed to accomplish the following transformations

( 8 ) Fill in the compounds in the following roadmap (only show the major product for each step)

1 ) (H 2 C=CH) 2 CuLi 2 ) CH 3 MgBr 1 ) O 3 2 ) Jones

1 ) DCC

1 ) PCC

2 ) NaOH, Me 2 SO 4

( 7 ) In the last question, why isn't the imine below the product?

HN

N

H

O

O N

O

O

O

CH 2 NH 2

OH

HO

O

H 3 CO

H

P

O

CH 3

O

EtO EtO NaOH H 3 CO

H

O

H 3 CO

HO

H 3 CO

O

HO

H 3 CO

O

O

OH

The enamine isomer has an aromatic ring and hence it is more stable 1 ) NaBH 4 2 ) PBr 3 3 ) NaCN 4 ) LiAlH 4 (LAH)