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Aldehyde and Ketones - Unsolved Problems | CHEM 212, Assignments of Organic Chemistry

Material Type: Assignment; Class: Organic Chemistry II; Subject: Chemistry; University: Bucknell University; Term: Unknown 1989;

Typology: Assignments

Pre 2010

Uploaded on 08/18/2009

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O
HO OH
O
HS SH
O
O
O
N
H
H
O
H
O
H
O
H
OHO OH
O
Br
O
O
O
Provide the products for the following reactions. Also show a complete mechanism for each transformation.
Clearly show every bond making and bond breaking step
H+ catalyst
O
EtOH
Br OMe
OMe
MeNH2
EtOH
MeNH2
OH
OH
1. NaBH4
2. H3O+
O
O
Ph3PO
pH 4.5
O
HCN
cat. NaOH
Br
1. NaNH2
2.
3. H3O+
Ph
O
acetone
1. PhMgBr
2. H3O+
3. PCC
4. MeOH, H+ catalyst
1. Ph3P
2. BuLi
3.
Chem 212
Aldehyde & ketone problems 1
H2NNH2, NaOH
H2O, heat
OH
OH
pH 4.5
H+
pH 4.5
N
H
NH2
1. Ph3P
2. BuLi
3. 2-pentanone
H
O
pH 4.5
NH2
NH2OH
pH 4.5
pH 4.5
Br
O1. MeOH, H+ catalyst
2. Mg
3. acetone
4. H3O+
H+ catalyst
H+ catalyst H+ catalyst
H+ catalyst
H+ catalyst

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O

HO

OH

O

HS

SH

O

O

O

N

H

H

O

H

O

H

O

H

O

HO

OH

O

Br

O

O

O

Provide the products for the following reactions. Also show a complete mechanism for each transformation. Clearly show every bond making and bond breaking step

H+^ catalyst

O

EtOH

Br OMe

OMe

MeNH (^2)

EtOH

MeNH

OH

OH

  1. NaBH (^4)
    1. H3 O+

O

O

Ph 3 P O

pH 4.

O

HCN

cat. NaOH

Br

  1. NaNH 2

3. H3 O+

Ph

O

acetone

  1. PhMgBr
  2. H 3 O+

3. PCC

  1. MeOH, H+^ catalyst

  2. Ph 3 P

  3. BuLi

Chem 212 Aldehyde & ketone problems 1

H 2 NNH2, NaOH

H 2 O, heat

OH

OH

pH 4.

H+

pH 4.

N

H

NH 2

  1. Ph (^) 3P
  2. BuLi
  3. 2-pentanone

H

O

pH 4.

NH 2

NH 2OH

pH 4.

pH 4.

Br

O 1. MeOH, H

  • (^) catalyst
  1. Mg
  2. acetone
  3. H3O+

H+^ catalyst

H+^ catalyst H^

  • (^) catalyst

H+^ catalyst

H +^ catalyst