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Practice Problems For Chapter 3: CH CH CHCH CH CH C (CH) CH CH

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Practice Problems for Chapter 3 1. Name the following compounds using IUPAC nomenclature.

2 9 8 7 6 5 4 1

CH 2CH 3
3

CH 3CH 2CHCH 2CH 2CH 2C(CH 3)2 Br


5

7-bromo-3,3-dimethylnonane

CH2CH3
1 2

CH3

4 3

Cis -1-ethyl-3-methylcyclopentane 2. Name the functional groups in the compound at right and draw an arrow from each functional group to its appropriate name
O C H2N carbonyl group O C OH double bond carboxyl group

amino group

3. Draw all nine of the constitutional (structural) isomers of C7H16 in skeletal form 1
C6 +C1 2-methylhexane 3-methylhexane

C5+C1+C1 3,3-dimethylpentane

2,3-dimethylpentane C4+C1+C1+C1

2,4-dimethylpentane

2,2-dimethylpentane

2,2,3-trimethylbutane C5+C2

3-ethylpentane

4. Show the general structure for each functional group below


R = generic alkyl group a) amine R NH2 d) ether R O R b) ester R O R c) aldehyde R H O e) carboxylic acid R C O H f) nitrile R C N O C O C

5. Draw all the structural isomers for alcohols with the formula C5H12O.
alcohols contain the -OH functional group C 5+OH HO CH 2CH 2CH 2CH 2CH 3 C 4+C 1+OH OH CH 3 C CH 2CH 3 CH 3 C 3+C 1+C 1+OH CH 3 CH 3 C CH 2-OH CH 3 OH CH 3 CH CHCH 3 CH 3 CH 3 HO CH 2CH 2CHCH 3 HO CH CHCH CH 2 2 3 CH 3 OH OH

CH 3 CHCH 2CH 2CH 3 CH 3CH 2 CHCH 2CH 3

6. Name the following compounds using IUPAC nomenclature.


CH3 CH2CH3 CH2CH3
6 8 7 4 5 3

CH3CHCHCH2CHCH(CH3)2

3-ethyl-2,5,6-trimethyloctane
CH 3 H H CH 2CH 3

trans-1-ethyl-3-methylcyclohexane

7. Label the carbons in the structure at right as either 1, 2, 3 or 4


2 2 2 1 2 3 4 3 2 2 1

8. Circle each functional group in the structure, below, and connect the circle to the name for the functional group.
cyano group carbonyl group N carboxylate O group C CH3 O oxo group C O double bond O N O CH2 NH CH3 OH O hydroxyl group C OH amino group amido group

carboxyl group

9. Show the IUPAC name for the structure at right.


8 7 CH 3CHCH 3 CH 3

CH 3CHCH 2CH 2CCH 2CH 3 3 6 5 4 CH 3CHCH 3 2 1

3-ethyl-2,3,6,7-tetramethyloctane

10. Identify each carbon, in the structure at right, as 1, 2, 3, or 4.


2 2 2 2 1 3 4 1 1 2

11. Draw, below, all the structural isomers for bromoalkanes with the formula C5H12Br.
C 5+Br Br C 4+C 1+Br Br Br C 3+C 1+C 1+Br Br Br Br Br

Br

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