Chemistry 52 ANSWER KEY REVIEW QUESTIONS Chapter 19 1. Circle and identify each functional group in the structures below: Alcohol Ester Acid Alcohol Alkene Ketone Aldehyde Ester Amine
Amide 1 2. Identify the functional groups and draw stick diagrams for each structural formula shown below: a) acid O H 3 C OH NH 2 amine b) O O H 3C H 3 C ester alcohol H 3 C 3. Name each of the following alkanes using the IUPAC system: a) 2­methylbutane b) 2,2­dimethylpropane c) 2,3­dimethylpentane d) 4­ethyl­2,2­dimethylhexane 2 OH 4. For each stick diagram shown below, write condensed structural and molecular formulas and name using the IUPAC system: a) H 3 C CH 3 Molecular formula: CH 3 Structural formula: Name: CH 3 b) 3­methylhexane CH 3 H 3 C Molecular formula: CH 3 C10H22 Structural formula: Name: H 3 C C7H16 4­ethyl­2­methylheptane CH 3 c) CH 3 H 3 C CH 3 Molecular formula: C10H22 Structural formula: Name: d) 3,4,5­trimethylheptane Cl H 3 C Cl Molecular formula: H 3C C6H12Cl2 CH 3 Structural formula: Name: 3 2,4­dichloro­3­methylpentane 5. Write the condensed structure for each of the following: a) 3­ethylhexane b) 2,3­dimethylpentane c) 1,3­dichloro­3­methylpentane 6. For each hydrocarbon shown below, identify carbons and hydrogens as primary (1°), secondary (2°) or tertiary (3°). a) # 1°C: 3 # 2°C: 1 # 3°C: 1 # 1°H: # 2°H: 2 # 3°H: 1 # 1°C: 4 # 2°C: 1 # 3°C: 2 # 1°H: # 2°H: 2 # 3°H: 2 # 1°C: 5 # 2°C: 3 # 3°C: 1 # 1°H: # 2°H: # 3°H: 1
9 b) 12 c) 15 4 6 7. Complete each of the reactions shown below. If reactions produce more than one isomer, draw structure and name each isomer. a) hυ
CH3CH2CH2CH2CH3 + Br2 ¾¾
® (all mono­brominated products) CH3CH2CH2CH2CH2Br 1­bromopentane + 2­bromopentane + 3­bromopentane b) D
CH3CH2CH2CH2CH3 ¾¾
® CH3CH2CH2CH=CH2 + CH3CH2CH=CHCH3 c) hυ
CH3CH2CH2CH3 + Cl2 ¾¾
® (all di­chlorinated products) (excess) CH3CH2CH2CHCl2 1,1­dichlorobutane 2,2­dichlorobutane 2,3­dichlorobutane ClCH2CH2CH2CH2Cl 1,2­dichlorobutane 1,3­dichlorobutane 5 1,4­dichlorobutane
8. Indicate whether each of the following pairs of structural formulas represent isomers or the same molecule: a) Isomers b) Isomers c) Same molecule
6