ISOMERISM

Q1. Which of the following show geometrical isomerism? Write the structures for cis and trans
isomers.
(i) 2Methylprop1ene (ii) 1, 2Dichloroethene (iii) But2endoic acid
Q2. Assign (E) and (Z) configuration to the following:

Q3. Cycloalkane derivatives do not contain any double bond but still show geometrical isomerism.
Explain and illustrate.
Q4. What happens when acetaldehyde is treated with hydroxylamine? Assign configurations to the
isomers that are formed.
Q5. Account for the following:
(a) The dipole moment of the cis geometrical isomer is generally more than that of the trans
isomer.
(b) The m.p. of trans isomer is normally more than that of the cis isomer.
Q6. Assign R and S configurations to each of the following:

Q7. Give the examples of two compounds which exist as optical isomers in the absence of chiral
carbon atoms and give suitable explanation.
Q8. Optically active 2iodobutane on treatment with NaI in acetone gives a product which does not
show optical activity. Explain.
Q9. How many asymmetric carbon atoms are created during the complete reduction of benzyl
(PhCOCOPh) with LiAlH4? Also write the number of possible stereoisomers in the product.
Q10. Mark the chiral carbon atoms and give the total number of stereoisomers in the following
compounds:
(i) CH3(CHOH)2COOH (ii) HOOC(CHOH)2COOH
(iii) CH3CHOHCOOH (iv) HOH2C(CHOH)4CHO
Q11. Out of but1yne and but1ene which has more dipole moment?
Q12. Addition of bromine to cisbut2ene gives a racemic mixture while addition to
transbut2ene will yield a meso molecule. Explain.
Q13. Which isomerism is exhibited by the following?
OH O

and

Q14. Give all the structural isomers for the molecular formula C6H14 and give their IUPAC names.
Q15. Which type of structural isomerism is shown by the following pairs?
O O
(i) ||
and ||
CH 3  C  OH H  C  OCH 3
(ii) CH 3  CH 2 C  CH and CH 3  C  C  CH 3
CH 3 CH CH 3
(iii) CH 3 CH 2 CH 2 NH 2 and |
NH 2

Q16. Give the structures of all the aromatic compounds represented by the molecular formula C7H8O.
Q17. Discuss in brief different conformations of:
(i) Ethane (ii) nbutane
Q18. Assign E or Z configuration to following:

Q19. Assign R or S configurations to following:

Q20. Designate R and S configuration to the following: