Chapter3 - Chapter 3 3.1 Identify the functional groups in...

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Chapter 3 3.1 Identify the functional groups in each of the following molecules: (a) C O NH 2 (b) N C OH O H (c) O O OCH 3 (d) H C CH 2 CH 2 OH Solutions: a. Amide, double bond b. Amine, carboxylic acid c. Double bond, ketone, ester d. Aromatic ring, double bond, alcohol 3.2 Propose structures for simple molecules that contain the following functional groups: (a) Alcohol (b) Aromatic ring (c) Carboxylic acid (d) Amine (e) both ketone and amine (f) two double bonds Solutions: (a). H 3 CO H (b). CH 3 (c). H 3 C OH O (d). H 3 CN H 2 (e). CH 3 CH 2 COCH 2 CH 2 NH 2 (f). 3.3 Identify the functional groups in the following model of arecoline, a veterinary drug used to control worms in animals. Convert the drawing into a line-bond structure and a molecular formula.
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Solution: Line-bond structure: Molecular formula: C 8 H 13 NO 2 3.4 Draw structures of the five isomers of C 6 H 14 . Solution: 3.5 Propose structures that meet the following descriptions: (a) Two isomeric esters with the formula C 5 H 10 O 2 (b) Two isomeric nitriles with the formula C 4 H 7 N Solution: (a): C O O H 3 C H 2 C C H 2 CH 3 H 2 C C H 3 C O C H 2 CH 3 O (b): CN C H 2 H 2 C H 3 C CH H 3 C H 3 C
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3.6 How many isomers are there with the following descriptions? (a) Alcohols with the formula C 3 H 8 O (b) Bromoalkanes with the formula C 4 H 9 Br Solution: (a): OH OH (b):4 3.7 Draw the eight 5-carbon alkyl groups(pentyl isomers). Solution H 2 C C H 2 H 2 C C H 2 CH 3 H 3 C CH C H 2 H 2 C CH 3 H 3 C H 2 C CH H 2 C CH 3 C H 2 H 2 C CH CH 3 H 3 C CH CH CH 3 H 3 C H 2 C C CH 3 H 3 C C H 2 CH C H 2 H 3 CC H 2 C CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 3.8 Identify the carbon atoms in the following molecules as primary, secondary, tertiary, or quaternary: Solution: (a) H 3 H H 2 C H 2 C CH 3 CH 3 1 1 1 2 2 3 (b) H 3 C H 2 C C H H 2 C CH 3 H C CH 3 H 3 C 1 1 1 1 2 2 3 3 (c)
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C H H 2 C C CH 3 CH 3 CH 3 H 3 C CH 3 4 1 1 1 1 1 2 3 3.9 Identify the hydrogen atoms on the compounds shown in Problem 3.8 as primary, secondary, or tertiary. Solution: The hydrogen in red is primary hydrogens; in blue is secondary hydrogens; in green is tertiary hydorgens (a) C H 3 C H C H 2 C H 2 C H 3 C H 3 (b) C H 3 C H 2 C H C H 2 C H 3 H 3 CC H C H 3 (c) C H 3 C H C H 2 CC H 3 C H 3 C H 3 C H 3 3.10 Draw structures of alkanes that meet the following descriptions: (a) An alkane with two tertiary carbons (b) An alkane that contains an isopropyl group (c) an alkane that has one quaternary and one secondary carbon Solution: (a) CH 3 CHCHCH 3 CH 3 CH 3 (b) CH 3 CHCH 2 CH 3 CH 3 CH 3 CCH 2 CH 3 CH 3 CH 3 3.11 Give IUPAC names for the following compounds: (a) The three isomers of C 5 H 12 (b) H 3 CH 2 CC H CHCH 3 CH 3 CH 2 CH 3 (c) (H 3 C) 2 HCH 2 H CH 3 CH 3 (d) (H 3 C) 3 CH 2 2 H CH 3 2 CH 3
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Solution: (a) CH CH CH CH CH Pentane H 3 CH 2 CC H CH 3 CH 3 2-Methylbutane H 3 CH 3 CH 3 CH 3 2,2-Dimethylpropane (b) 3,4-Dimethylhexane (c) 2,4-Dimethylpentane (d) 2,2,5-Trimethylheptane 3.12 Draw structures corresponding to the following IUPAC names: (a) 3,4-Dimethylnonane (b) 3-Ethyl-4,4-dimethylheptane (c) 2,2-Dimethyl-4-propyloctane (d) 2,2,4-Trimethylpentane Solution: (a) (b) (c) (d) 3.13 Name the eight 5-carbon alkyl groups you drew in problem 3.7.
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Chapter3 - Chapter 3 3.1 Identify the functional groups in...

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