MOLECULAR REPRESENTATIONS AND INFRARED SPECTROSCOPY

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1 MLEULAR REPRESENTATINS AND INFRARED SPETRSPY A STUDENT SULD BE ABLE T: 1. Given a Lewis (dash or dot), condensed, bond-line, or wedge formula of a compound draw the other representations. 2. Give examples of, and recognize when given the structure, representatives of the following classes of compounds. Also, draw isomers of given compounds. ydrocarbons (compounds containing and only) Saturated - alkanes Unsaturated - alkenes (olefins), alkynes, aromatics rganic compounds containing halogens Alkyl halides (1 o, 2 o, 3 o ) ompounds containing oxygen: - single bonds only: alcohols (1 o, 2 o, 3 o ), ethers = compounds: aldehydes, ketones, carboxylic acids, esters, acyl halides, anhydrides ompounds containing nitrogen: amines (1 o, 2 o, 3 o ), amides, nitriles ompounds containing sulfur: thiols, sulfides 3. Identify functional groups present in molecules from infrared (IR) spectroscopy data, and predict features of the IR spectrum of molecules from their structures. Important IR absorption frequencies to know include: (alcohols, hydrogen bonded): cm -1, strong and broad N-: cm -1, medium intensity (carboxylic acids): cm -1, broad peaks of variable intensity =: cm -1, strong absorption If you need to use other frequencies to identify other functional groups (and sometimes you will), a table of IR frequencies will be provided. 4. Apply concepts learned in Module 1.

2 Simplified Table of Main IR Frequencies Wave number, cm -1 Functional Group Peak Description (alcohol) Strong and broad (carboxylic acids) Very broad (over ~ 500 cm -1 ), often looks like distorted baseline, can reach above 3000 cm N- Doublet in case of N 2 group of a primary amine or amide terminal alkyne alkene or arene Usually sharp and s trong ften weak, overlaps with alkane absorption (sp 3 carbon) Strong, broad and multi-banded N alkyne Medium intensity Medium intensity for terminal alkynes, very weak for internal = Very strong; (amides, ketones, aldehydes lower frequency for amides and carboxylic acid, esters) when = is conjugated = heck to see if you have - alkene, aromatic ring unsaturated >3000 cm -1 (if not, it s completely substituted) ~ N 2 (bending) nly if you have corresponding N- 1 amines and amides peak at cm -1 (this peak may be mistaken for = otherwise) 1200 Ar- Strong (look for =- & = first) and 750 phenyl group Strong (look for =- & = first)

3 To best prepare for this module, please work hapter 2 Skill Builder problems and hapter 15 Skill Builder problems (IR problems only) in the textbook. A STUDENT W AS MASTERED TE BJETIVES FR TIS UNIT SULD BE ABLE T SLVE TE FLLWING PRBLEMS AND RELATED NES: 1.1 Draw complete structures (showing all atoms, bonds as lines, and non-bonding valence electrons as dots) for the following compounds: a) ( 3 ) b) 3 ( 2 ) 3 3 c) d) Draw a bond-line structure for each of the following compounds. Use dashes and wedges to indicate three-dimensional geometry where appropriate. a) ( 2 5 ) 3 ( 2 ) 2 ( 2 5 )( 3 )( 2 ) 2 3 b) (3 ) 2 ( 3 )( 2 ) 2 ( 2 5 )( 2 ) 2 3 c) d) e) ( 3 2 ) 3 ( 2 ) 2 ( 2 ) 2 ( 2 3 ) 3 f) ( ) N

4 1.3 Draw both condensed and bond-line structures for (a) and (b); draw a bond-line formula for (c). \ / a) b) l c) = / \ = / \ 1.4 Draw condensed formulas for each of the following. a) b) S c) d) S 2.1 Draw the structure of an example of each of the following classes of compounds. Do not use the symbol R. a) alkane b) ether c) 2 o amine d) 3 o alcohol e) aldehyde f) 1 o alkyl halide g) thiol h) alkyne i) acyl chloride 2.2 Name the functional group or groups in each of the following molecules. Indicate 1 o, 2 o, or 3 o where appropriate. a) b) c) 3

5 2.2 (ontinued) d) N e) 3 3 f) g) h) S i) 3 2 -S Based on the IR data given, what functional group(s) can be present in these compounds? a) A strong absorption at 1710 cm -1, no N in the molecular formula, no - peaks present. b) A strong absorption at 1720 cm -1 and a broad absorption between cm -1. c) An oxygen-containing compound with a strong absorption at cm -1, no N in the molecular formula, no peak at cm An oxygen-containing compound does not have IR peaks in either the cm -1 region or the cm -1 region. Which of the following general formulas fits this IR spectrum? A. R B. R. RR D. RR 3.3 For each of the following compounds, determine whether or not you would expect its IR spectrum to exhibit a signal to the left of (a) (b) N (c) N 2 (d) (e) (f)

6 3.3 ontinued. (g) (h) 3.4 What IR frequencies would enable a chemist to distinguish between these? a) 3 2 and b) c) and and An unknown compound having the formula 6 13 N had a peak in its IR spectrum at 3350cm -1. Which of the following compounds is consistent with this? 3 A. B.. D. N N For each of the following IR spectra, identify whether it is consistent with the structure of a ketone, an alcohol, a carboxylic acid, a primary amine, or a secondary amine. Explain your answer. (a)

7 3.6 (ontinued) (b) (c) 4.1 Draw all constitutional isomers of 3 9 N and identify the functional group present in each one. Indicate 1 o, 2 o, and 3 o if appropriate. 4.2 Which of the following compounds is most soluble in water? Which is most soluble in hexanes? (a) 3 2 N 2 (b) 3 ( 2 ) 2 (c) 3 ( 2 ) 3 3 (d) ( 2 5 ) 2 2 Br

8 4.3 Which compound has the highest boiling point? Which has the lowest? A. ( 3 2 ) 3 N B.. D S Provide hybridizations and approximate bond angles around the atoms that are in bold. You may need to add lone pairs to complete the octet. (a) 3 S (b) ( 3 ) 2 N- 2 - N hybridization bond angle

9 SLUTINS T SAMPLE PRBLEMS: 1.1 Draw complete structures: a) b) c) d) 1.2 Draw a bond-line structure: a) b) c) d) e) f) N

10 1.3 a) b) l( 2 ) 2 ( 3 ) 2 c) l 1.4 ondensed formula: a) 2 ( 3 )()( 2 ) 2 ( 3 ) b) ( 2 5 ) 2 ( 2 ) 3 3 c) ( 3 ) 2 (S) ( 3 ) 3 d) ( 3 ) 2 2 S( 2 ) 2 ( 2 5 ) ( 3 ) There are numerous other correct answers. These are just examples. a) alkane b) ether c) 2 o amine N 2 3 d) 3 o alcohol e) aldehyde f) 1 o alkyl halide Br g) thiol h) alkyne i) acyl chloride S l 2.2 a) alkene b) aromatic, carboxylic acid c) aromatic ring, ketone d) amide e) 2 o alcohol, alkyne f) ester g) aromatic ring, anhydride h) thiol i) sulfide 3.1 a) Aldehyde, ketone, ester, anhydride b) arboxylic acid c) alcohol 3.2 D 3.3 (a) no (b) no (c) yes (d) no (e) yes (f) yes (g) yes (h) no

11 3.4 (a) cm -1 () (b) (=) (c) (=-) 3.5 A 3.6 (a) primary amine (3500 cm -1 ) (b) alcohol (broad band 3350 cm -1 ) (c) ketone (=, near 1700 cm -1 ) N 2 3 N N 3 3 N 3 primary amine primary amine secondary amine tertiary amine 4.2 A is most soluble in water; is most soluble in hexanes 4.3 B has the highest bp; has the lowest bp 4.4 (a) 3 S (b) ( 3 ) 2 N- 2 - N hybridization sp 3 sp 3 sp 2 sp 2 sp 3 sp bond angle o o 120 o 120 o o 180 o

12 Name Second Drill Test (Sample A) rganic hemistry 2210 DR Answer All Questions 1. Name the functional group in each of the following compounds, indicating 1, 2, or 3 if appropriate. (a) (b) 3 N 3 (c) ( 3 ) Give specific examples (do not use R) for each of the following types of compounds. a) 3 alcohol b) ester c) aldehyde d) sulfide 3. Which of these compounds has a peak in its IR spectrum nearest 3030 cm -1? A. B. =. D. 4. Which of the following functional groups does not show any absorption bands in the cm -1 region of the infrared spectrum? A. alcohols B. primary amines. secondary amines D. tertiary amines 5. What IR frequencies would enable a chemist to distinguish between these? ( 3 2 ) 3 N and ( 3 2 ) 2 N 6. Which of the following compounds has the highest boiling point? A B D Which of the following compounds is most soluble in water? Which is most soluble in hexanes? A S- 2 3 B. 3 ( 2 ) D. 3 ( 2 ) 5 2 Br

13 Name Second Drill Test (Sample B) rganic hemistry 2210 DR Answer All Questions 1. Draw structures as indicated. (a) Lewis structure of (b) an isomer of N B (c ) condensed formula for (d) a bond-line formula for 3 ( 2 ) 3 ()=( 3 ) 2 2. onsider the molecule below. Give: (a) the hybridization of 2 (b) the hybridization of 4 (c) the -4-5 bond angle 3. Draw the structure of an example (do not use R) of each of the following classes of compounds. (a) 1 o amine (b) acyl chloride (c) ether (d) 2 o alkyl bromide 4. Name the functional group or groups present in each of the following molecules. Indicate 1 o, 2 o, or 3 o when appropriate. (a) N- (b) N (c) S

14 5. Multiple hoice (1) An oxygen-containing compound which shows no IR absorption at cm -1 or cm -1 is likely to be what type of compound? (A) an amide (B) an alcohol () a ketone (D) an ether (2) Which of these compounds has a peak in its IR spectrum at cm -1? (A) (B) () (D) (3) Which of the following compounds has the highest boiling point? (A) (B) () (D) (4) Which of the following compounds is least soluble in water? (A) Br () ( 3 ) (B) (D) ( 3 ) Br 6. Indicate which of the four compounds below is responsible for the IR spectrum shown below. Explain your answer.

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