organic solution mj

8/11/2019 Organic Solution Mj

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1.

When two moles of oxaldehyde are heated with NaOH, they undergo intermolecular cannizaro

reaction to give equimolar amounts of corresponding alcohol and the salt of carboxylic acid.

2.

Compound

O

O

react with 2 moles of Grignard reagent to giveOH

OH

OO CH3MgBr

O OO

O1. CH3MgBr

2. H3O

OH

3.

CH3CH2CHO contain alpha hydrogen, when treated with NaOH; undergo aldol condensation

reaction to give alpha-beta unsaturated aldehyde.

4.

Two moles of cyclohexanone undergo aldol condensation reaction to give alpha-beta

unsaturated ketone.


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O

OH

O

O

OHO

H2O -H2O

O

5.

A is CH3CO2C2H5, an ester, containing alphahydrogen, when treated with strong base NaOC2H5

(B) undergo Claisen condensation reaction to give beta-keto ester which when hydrolysis form

beta-keto acid, which easily decarboxilate on heating to give acetic acid.

6.

When CH3CH = CHCHO is treated with NaOH , proton abstraction take place from methyl group

which is more acidic centre, and then undergo aldol condensation reaction.


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7. When CH3CH2OCOOCH2CH3is treated with two moles of methyl magnesium bromide form acetone.

The compound containing CH3CO- group gives positive iodoform test.

So acetone gives a ppt. of CHI3and carboxilate ion.

Acetone can also be obtained by ozonalysis of 2, 3-dimethyl-2-butene.

Further addition of methyl magnesium bromide gives tertiary alcohol after hydrolysis.

O O

O

CH3MgBr O O

OBrMg

O

O

CH3MgBr

O

OBrMgO

Acetone

O

CH3MgBr O

MgBrOHH3O

OzonalysisO O+

8. Under the influence of dilute base two molecules of aldehyde or ketone containing at least one alpha-

hydrogen undergo aldol condensation reaction.


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Compound

HC

CH3

CHO

contains alpha-hydrogen undergo aldol condensation reaction.

9. When Ethyl acetate is treated with ethoxide ion gives Claisen condensation product is Ethyl aceto

acetate (E.A.A) which gives positive iodoform reaction.

H3C C OEt

OOH

EtO C

O

CH2 OEtC

O

H3C+

EtO C

O

CH2 C OEt

O

CH3

EtO C

O

CH2 C CH3

O

When treated with NH2OH gives oxime.

EtO C

O

CH2 C CH3

O

+ NH2OH EtO C

O

CH2 C CH3

N

OH

E.A.A also undergo totomerisation

EtO C

O

C CH3

O

H

EtO C

O

CH2 C CH3

O

10.


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C NH2

OP5O10

NCH3MgBr

H3OC CH3

O

Ca(OH)2I2

C OH

O

+ CHI3Heat

A B

CD

11. When R-CO-NH2is treated with alkaline solution bromide undergoes Hofmann rearrangement

thorough following intermediates.

C NH2

O

ROH

C NH

O

RBr Br

C NHBr

O

R

C NBr

O

R

H OH

C NBr

O

R C

N

O

R Br -Br

R shiftR N C O

.

12. An unstable amide undergoes Hofmann degradation reaction when treated with alkaline solution

bromide. So CH3CONH2will show Hofmann degradation reaction.

13. A beta-keto acid decarboxilate readily on heating because the activation energy of this

decarboxilation, which involves a stable six-member cyclic transition state.

O OH

OH

O O


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14. Cyclohexanone, when treated with Ethyl aceto acetate in presence of ethoxide ion form

O O

O O

H3C C OEt

O O O

OEt

O O

OEt

15. Compound

H3C C O

OHC

CH3

Et*

undergoes hydrolysis through BAL1 mechanismwhere configuration of chairal carbon is retained.

H3C C O

OH

C

CH3

Et

Slow

H3C C O

O

+ HC

CH3

Et H2O

H3C C O

O

+ HC

CH3

Et

OH2

fast

H3C C OH

O

+ HC

CH3

Et

OH

*

*

**

16. When compound H3C CH2

C

H2

C C

H2

C CH3

O O

O is treated with one mole of ethyl

magnesium bromide form

O

OH3C

C2H5


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H3C C

H2C

H2C C

H2C CH3

O O

O

C2H5MgBr

H3OH3C C

H2C

H2C C

H2C CH3

OH

O

C2H5 O

O O

OCH2CH3

H3C

C2H5

OO

H3C

C2H5

17. When Ethyl acetate is treated with ethoxide ion undergoes Claisen condensation reaction to give

ethyl aceto acetate (E.A.A) which gives positive iodoform reaction.

H3C C OEt

OOH

EtO C

O

CH2 OEtC

O

H3C+

EtO C

O

CH2 C OEt

O

CH3

EtO C

O

CH2 C CH3

O

Enolic form of E.A.A decolorize Br2solution due presence of unsaturation

EtO C

O

C CH3

O

H

EtO C

O

CH2 C CH3

O

EtO C

O

CH

C CH3

OAc

EtO C

O

CH C CH3

OH

Br Br

Br2


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Enolic form of E.A.A also undergoes acylation when treated with acetic anhydride.

EtO C

O

C CH3

O

HAc2O

EtO C

O

CH

C CH3

OAc

18. Alkaline hydrolysis is maximum where the -NO2 group is at para position of the benzene ring,

because the electrophilicity of carbonyl carbon increases due toR effect of the -NO2 group.

19. Compound (I) is stabilized by the +R effect of OMe group whereas compound (II) is stabilized by

hyperconjugative effective of CH3 group (structre I). So (I) is most stable. In compound (III) positive

charge is delocalized into the phenyl ring only show less stability than previous compounds but more

stable than (IV) where positive charge is stabilized by only +I effect of methyl group.

20. Compound 3 is more stable as radical is fully delocalized into phenyl ring.


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21. Most stable radical is compound 4 as more delocalization of radical.

22. Most stable carbocation is compound 3 as positive charge is fully delocalized into phenyl ring.

23. Due to more electron density at Para position with respect to the -OCOPH group of the phenyl ring

electrophilic attack of -NO2group takes place at Para position of the phenyl group.

24. In compound (I) radical is stabilized by +R effect of phenyl ring whereas in compound (III) radical is

stabilized by three +I effect of methyl groups

In compound (II) radical is stabilized by hyper conjugation effect only and more than compound (IV).

So the order of stability is (IV) < (II) < (III) < (I).


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25. In SN2 fashion neucleophilic attack and leaving group departure occur simultaneously with inversion

of configuration of product.

C ClH

CH3

CH2CH3

C HCl

CH2CH3

CH3

OHC

H

Cl

CH2CH3

CH3

OH

C

H

CH2CH3

H3C Cl

C OHH

CH3

CH2CH3

organic solution mj

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