EMISTRY 10 elp Sheet # rganic (Part III hapters.7 (condensed, structural drawings, 6.3 (line drawings, 6.9a (benzene, 7.e (hybrid orbitals in organic structures, and Appendix E (functional groups Do topics appropriate for your lecture Prepared by Dr. Tony Jacob http://www.chem.wisc.edu/areas/clc (Resource page Nuggets: unctional Groups Part II, Naming and drawing organic molecules UNTINAL GRUPS unctional Group Suffix ormula ther Info single bonded always bent; polar; dipole-dipole functional groups Alcohol (anol R-- R ; 1,, 3 ; polar; -bonding; polar; 3 1 Naming: e.g., 3-methyl--butanol Ether --- R--R' R, R ; polar; alphabetize branches+ ether Naming: e.g., diethylether Aldehyde (anal carbonyl function groups R or R polar one must be attached to the carbonyl; pol 1 3 Ketone (anone R R' or R(=R Naming: e.g., 3-chloro-1-butanal R, R ; polar; l methyl 6 5 3 1 arboxylic acid (anoic acid Naming: e.g.,,5-dimethyl-3-hexanone R or R R R - + + R can be ; -bonding; polar; p < 7; acidic; methyl Ester R R' or R(R Naming: e.g., 3,3-dimethyl-1-butanoic acid 1 R can be ; R ; nice odors; R named 1 st + yl then R-(= named nd + anoate ; but + anoate ethyl 3 Amide --- R'' R N R' or R(NR R 3 1 1 Naming: e.g., ethylbutanoate R can be ; can have -bonding if R or R = ; N has sp hybridization rather than sp 3 because of resonance; hence triangular planar for both and N; planar; naming amides not usually covered - N + N sp sp 3 sp sp Amine --- NRR'R" (1 R must 1,, 3, (+1; can have -bonding; polar; p > 7; basic; NR 3 + NR 3 + + - alphabetize branches+ amine ; Naming: e.g., ethylmethylamine N( 3 ( 3
TER INRMATIN N Primary (1 alcohol: with (labeled has 1 attached (labeled as Primary (1 amine: N has 1 attached (labeled as N Secondary ( alcohol: with (labeled has s attached (labeled as Secondary ( amine: N has s attached (labeled as N Tertiary (3 alcohol: with (labeled has 3 s attached (labeled as Tertiary (3 amine: N has 3 s attached (labeled as SLUBILITY (re-visited: Liquids dissolving into liquids = miscibility (page 565-567: In general: Like likes Like polar substances dissolve into polar substances (dissolve = miscible; nonpolar substances (e.g., hydrocarbons! dissolve into nonpolar substances (dissolve = miscible; polar and nonpolar substances don t dissolve into one another (doesn t dissolve = immiscible more -bonding more soluble unctional Groups Alcohol: a (hydroxyl group attached; condensed: R ; -bonding primary (1 : with has 1 atom attached secondary ( : with has atoms attached tertiary (3 : with has 3 atoms attached to it Ether: bridging oxygen atom; condensed: R R'; R and R' otherwise it becomes an alcohol arbonyl unctional Groups ( Aldehyde: contains a carbonyl with at least one attached to of carbonyl; condensed: R; line: Ketone: a carbonyl with two attached; condensed: R R or R(=R ; line: R and R' otherwise it s an aldehyde arboxylic acid: a carbonyl with a attached; condensed: R; line: acidic solution (p < 7; + can dissociate: R R the - group (carboxylate has a resonance structure: - R R' ; R ; R can be a ; + ; has -bonding; - + Ester: condensed: R(R ; line: R R' ; R' otherwise it s a carboxylic acid; esters smell pleasant R'' Amide: condensed: R(=NR R ; line: R N R' ; R, R can be ; -bonding Amine: N with a attached to it; condensed: NRR'R"; -bonding; creates basic solution (p > 7 primary (1 : N has 1 attached secondary ( : N has attached tertiary (3 : N has 3 attached - R 1. Draw the following condensed molecular structures in a the Lewis dot format, b line notation, and c wedge-dash 3D structures. I. 3 ( 3 II. 3 III. ( 3 IV. 3 ( 3
. ircle each functional group present and name it. If it is an alcohol or amine functional group identify it as a 1,, or 3 alcohol or amine. If there is an alkene present, identify it as a cis, trans, or neither isomeric version. (int: There are 13 functional groups in the molecule. N N 3. Give the IUPA name for each of the following molecules. (Skip if naming not covered l l l l a. b. c. l N d. e. f. g. h.. Using line notation, draw the molecules given their names. a. -butanone b. 3,3-diethyl-1-pentanal c. -methyl-1-butanoic acid d. -ethyl-1-hexanoic acid e. cis-,6-dimethyl-3-heptene f. 3-ethyl--methyl--pentanol g. pentylpropanoate h. ethylethanoate i.,-dimethyl-3,3-dichloro--heptanone j. 3-tert-butyl-1-cyclohexanol k. 1-propanal l. ethylmethylether m. diethylisopropylamine
5. Give the IUPA name for each molecule. a. b. c. d. l e. f. g. h. i. j. k. l. 6. Write the condensed structures for the molecules given the names with bonds drawn between the groups (e.g., for ethane draw 3 3. a.,-dimethyl-1-propanal b. isopropanol c. 1,1,1-trichloro-3-pentanone d.,-diethyl-1-butanoic acid 7. Which of the following molecules are secondary alcohols? I. 1-butanol II. -pentanol III. 1-cyclopentanol IV. -methyl--butanol a. I, II, III, IV b. II, III, IV c. II d. II, III e. IV f. I 8. Place the following chemicals in order from low to high solubility in water. I. 3 ( 3 3 II. 3 ( 3 III. 3 a. I < II < III b. III < II < I c. II < III < I d. I < III < II e. III < I < II 9. Place the following chemical in order from low to high boiling point. I. 3 (( 3 II. 3 III. a. I < II < III b. III < II < I c. II < III < I d. I < III < II e. III < I < II
ANSWERS 1. I. a. b. c. II. a. III. a. b. c. b. c. IV. a. b. c. E A B D G N I N J L K. A: cis-alkene B: ester : ketone D: aldehyde E: alkene (neither cis nor trans : aromatic G: alcohol : amide I: 1 amine J: cyclic alkane (or just cyclic K: 3 alcohol L: carboxylic acid M: trans-alkene 3. a.,-dimethyl-1-propanol b.,3,,-tetrachloro-1-butanal (aldehydes is always on the 1st position; sometimes called:,3,,-tetrachlorobutanal c. 3-ethyl-3-pentanol d. -chloro-,-difluoro--butanone e. ethylisopropylamine f. ethanoic acid (common name: acetic acid g. 3,5-dimethyl-1-hexanoic acid (carboxylic acids is always on the 1st position; sometimes called: 3,5-dimethylhexanoic acid h. ethylpropanoate M
. a. b. c. d. e. f. g. h. i. l l j. N k. l. m. 5. a. trans-,5-dimethyl-3-hexene b. 1-butanal c. 3-ethyl--hexanol d.,-dimethyl-1-butanol e. -pentanone f. cis--hexene g. 3-chloro--ethyl--hexanone h.,-dimethylpentanal i.,-dimethylpentanoic acid j.,,-trifluoroethanoic acid k. methylbutanoate l. propylpentanoate 6. a. 3 ( 3 b. ( 3 ( or 3 ( 3 c. l 3 ( 3 d. 3 ( 3 7. d {I. 1 alcohol: II. alcohol: III. alcohol: IV. 3 alcohol: 8. a {for solubility, 1. polar substances dissolve into polar substances;. ions more readily dissolve into water; 3. molecules with -bonding more readily dissolve into water; } I: ; II: ; III: and - + + I. hydrocarbon: nonpolar low solubility in water; II. polar because of the carbonyl more soluble in water than molecule I; III. polar because of the carbonyl; also can dissociate to create an ion and ions are more soluble in water; can -bond to the water all of these increase the solubility of molecule III in water as compared to the other molecules} 9. e {as IMs increase boiling point increases; I: has -bonding in locations; II: has - bonding in 1 location; III: has -bonding in locations plus the in the group without the can also -bond to another molecule with the coming from the other molecule; hence more -bonding in molecule III}