Chemistry Guru :: Making Chemistry Simpler :: www.chemistryguru.com.sg INTRO TO ORGANIC CHEM PRACTICE 1.

. Give the IUPAC names of the following compounds

(a)

CH3

CH3

(b)

CH3CHCH2CHCH(CH3)2 Br
(d)

CH3CHCHCHCH2CH3 CH2CH3
(c)

Br CH2CH3

(CH3)3CCHCH3 CH2CH3

CH2CH3 CH3
(f)

(e)

OH BrCH2CH2CCH3

CH3CH2 H

H C C CHCH2CH3 CH3

(g)

H H3C CH2 C

I C

OH CH CH2 OH

(h)

NO2 H

H Br CH2 CH2 C C CH3 H CH3

Cl

2. Write structural formula for the following compounds (a) 2,3-dimethylpentane (b) 2-ethyl-1,1-dimethylcyclobutane (c) 3-ethyl-2,4-dimethylhexane (d) 1-bromo-5-chloro-4,4-dimethylheptane (e) 3-ethyl-5-methylhepta-1,5-diene (f) cis-hex-3-ene-3-ol 3. Which of the following compounds can exist as pairs of cis-trans isomers? If so, draw and name the isomers. (a) CH3CH=CH2 (b) CH3CH2CH=CHCH3 (c) ClCH=CHCl 4. Draw and give the IUPAC name of the all isomers of butanol, C4H7OH

5. Mark all chiral centres for the following compounds with asteriks and determine the total number of stereoisomers. For (a) and (b), draw the mirror images of the enantiomers. (a) CH3CH(NH2)COOH (b) CH3CHClCH2CH3 (c) (d)

H3C

Br

CH2Br

Br

CH3

Chemistry Guru :: Making Chemistry Simpler :: www.chemistryguru.com.sg 6. Classify the following reactions, eg addition, elimination, substitution, condensation, hydrolysis, oxidation, reduction.
H H H3C C C CH3 H H

H Cl

H3C C C CH3 H Cl

(a)

H3CCH2CH2Br
(b)

alc.KOH

H3C C H

CH2

+ HBr

(c)

H3C CH3 OH
O

conc. H2SO4
H+ H2O O

H2C CH2

+ H2O

(d)

H3C C NH2 +

H3C C OH

NH4+

(e)

CH3CH2 OH CH3-CO-CH3 CH3CH2Cl

CH3-COOH

(f)

CH3CH(OH)CH3 CH3CH2OH

(g)