Problem 1 C5H10O MW 86 The band at 1716 indicates a carbonyl, probably a ketone.

The bands at 3000-2850 indicate C-H alkane stretches.

Problem 1, NMR intrepreted

Problem2 C7H14O MW 114 The band at 1718 indicates a carbonyl, probably a ketone. The bands at 3000-2850 indicate C-H alkane stretches.

Prob 2 NMR, interpreted

Problem 3 C4H10O MW 74 The broad band at 3339 indicates O-H stretch, probably an alcohol. The bands at 3000-2850 indicate C-H alkane stretches. The band at 1041 is C-O stretch, consistent with an alcohol.

Prob 3 NMR, interpreted

Problem 4 C6H14O MW 102 The broad band at 3350 indicates O-H stretch, probably an alcohol. The bands at 3000-2850 indicate C-H alkane stretches. The bands from 1320-1000 indicate C-O stretch, consistent with an alcohol.

Prob 4 NMR, interpreted

Note that the structure has a chiral center and the mixture is racemic. Methylene protons adjacent to a chiral center may not be identical.

Problem 5 C4H8O2 MW 88 Prob 5, IR answer The band at 1743 indicates a carbonyl, probably a saturated aliphatic ester. The bands at 3000-2850 indicate C-H alkane stretches. The bands in the region 1320-1000 could be due to C-O stretch, consistent with an ester.

Prob 5 NMR, interpreted

Problem 6 C5H10O2 MW 102 Prob 6, IR answer The band at 1740 indicates a carbonyl, probably a saturated aliphatic ester. The bands at 3000-2850 indicate C-H alkane stretches. The bands in the region 1320-1000 could be due to C-O stretch, consistent with an ester.

Prob 6 NMR, interpreted

Problem 7 C5H10O MW 86 Prob 7, IR answer The band at 1728 indicates a carbonyl, probably an aldehyde; an aldehyde is also suggested by the band at 2719 which is likely the C-H stretch of the H-C=O group. The bands at 3000-2850 indicate C-H alkane stretches.

Prob 7 NMR, interpreted

Problem 8 C8H8O MW 120 Prob 8, IR answer The band at 1703 indicates a carbonyl; that the carbonyl is an aldehyde is suggested by the bands at 2828 and 2733 (C-H stretch of the H-C=O group). The bands at 3000-2850 indicate C-H alkane stretches. The band (unmarked on the graph below) just to the left of 3000 indicates aromatic C-H stretch. Aromatics also show bands in the regions 1600-1585 and 1500-1400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane).

Prob 8 NMR, interpreted

Note: There are 4 aromatic protons (B, 7-8 ppm), indicating a disubstituted aromatic ring. You are not expected to assign the individual peaks in the aromatic region to specific hydrogens on the aromatic ring. The aromatic protons show a pattern characteristic of para substitution.

Problem 9 C9H10O2 MW 150 Prob 9, IR answer The band at 1697 indicates an alpha, beta-unsaturated carbonyl; that the carbonyl is an aldehyde is suggested by the bands at 2828 and 2739 (C-H stretch of the H-C=O group). The bands at 3000-2850 indicate C-H alkane stretches. The band (unmarked on the graph below) just to the left of 3000 indicates aromatic C-H stretch. Aromatics also show bands in the regions 1600-1585 and 1500-1400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane).

Prob 9 NMR, interpreted

Problem 10 C3H6O2 MW 74 Prob 10, IR answer

The band at 1716 indicates a carbonyl. The wide band from 3300-2500 is characteristic of the O-H stretch of carboxylic acids. The bands at 3000-2850 indicate C-H alkane stretches. The bands in the region 1320-1000 indicate the C-O stretch of carboxylic acids.

Prob 10 NMR, interpreted

Problem 11 C11H14O2 MW 178 Prob 11, IR answer The band at 1684 indicates a carbonyl. The wide band from 3300-2500 is characteristic of the O-H stretch of carboxylic acids. The bands at 3000-2850 indicate C-H alkane stretches. The bands in the region 1320-1000 indicate the C-O stretch of carboxylic acids. The band (unmarked on the graph below) just to the left of 3000 indicates aromatic C-H stretch. Aromatics also show bands in the regions 1600-1585 and 1500-1400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane).

Prob 11 NMR, interpreted

Problem 12 C8H8O2 MW 136 Prob 12, IR answer The band at 1684 indicates a carbonyl. The wide band from 3300-2500 is characteristic of the O-H stretch of carboxylic acids. The bands at 3000-2850 indicate C-H alkane stretches. The bands in the region 1320-1000 indicate the C-O stretch of carboxylic acids. The band just to the left of 3000 (3065) indicates aromatic C-H stretch. Aromatics also show bands in the regions 1600-1585 and 1500-1400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane).

Prob 12 NMR, interpreted

Problem 13 C7H9N MW 114 Prob 13, IR answer The two bands at 3433 and 3354 indicate a secondary amine. The bands at 3000-2850 indicate C-H alkane stretches. The band at 3034 indicates aromatic C-H stretch; aromatics also show bands in the regions 1600-1585 and 1500-1400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane). C-N stretch of aromatic amines would show up at 1335-1250 (there is a band in that region).

Prob 13 NMR, interpreted

Problem 14 C5H13N MW 87 Prob 14, IR answer The two bands at 3388 and 3292 indicate a secondary amine. The bands at 3000-2850 indicate C-H alkane stretches.

Prob 14 NMR, interpreted

Problem 15 C8H14O MW 126 Prob 15, IR answer The band at 1718 indicates a carbonyl, probably a ketone. The bands at 3000-2850 indicate C-H alkane stretches. Since the compound is an alkene, one would expect to see C=C stretch at 1680-1640; these weak bands are not seen in this IR (according to Silverstein, "the C=C stretching mode of unconjugated alkenes usually shows

moderate to weka absorption at 1667-1640"). Since the compound is an alkene, C-H stretch should appear above 3000 (not seen: the absorption for this single hydrogen must be too weak).

Prob 15 NMR, interpreted

Problem 16 C4H9Br MW 137 Prob 16, IR answer The bands at 3000-2850 indicate C-H alkane stretches. The bands in the region 1300-1150 could indicate C-H wag (-CH2Br) of an alkyl halide.

Prob 16 NMR, interpreted

Problem 17 C10H14O MW 150 Prob 17, IR answer The bands at 3000-2850 indicate C-H alkane stretches; the small (unmarked) band just to the left of 3000 indicates aromatic C-H stretch. Aromatics also show bands in the regions 1600-1585 and 1500-1400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane). The wide band in the region 3500-3200 indicates the O-H stretch of an alcohol or phenol.

Prob 17 NMR, interpreted

Problem 18 C13H10O3 MW 214 Prob 18, IR answer The band at 1682 indicates a carbonyl, probably an ester. The band at 3192 indicates C-H aromatic stretch; aromatics also show bands in the regions 1600-1585 and 1500-1400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane). The wide band just to the left of the 3192 band indicates O-H stretch (alcohols and phenols).

Prob 18 NMR, interpreted

Note: the correct placement of the -OH on the ring and the arrangement of the ester may be beyond the scope of your spectroscopy course. See this explanation.

Problem 18, structure

Problem 19 C8H14 MW 110 Prob 19, IR answer The bands at 3000-2850 indicate C-H alkane stretches. There really aren't many other bands in the spectrum to indicate functional groups. The compound is an alkyne; we would expect to see a carbon-carbon triple bond stretch at 2260-2100, however, this is a weak band at best and often does not show up on IR.

Prob 19 NMR, interpreted

Note: The integral values for A, B, and C need to be multiplied by 2 to get a total of 14 protons in the molecule. By convention, integral values on an nmr are reported as the lowest common multiple.

Problem 20 C9H13N MW 135 Prob 20, IR answer The bands at 3000-2850 indicate C-H alkane stretches. The band at 3028 indicates C-H aromatic stretch; aromatics also show bands in the regions 1600-1585 and 15001400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane). The bands in the region 1250-1020 could be due to C-N stretch. The weak, broad banc at about 3500 could be amine N-H stretch or it could be a slight contamination of an impurity (water) in the sample.

Prob 20 NMR, interpreted

Problem 21 C9H10 MW 118 Prob 21, IR answer

The bands at 3000-2850 indicate C-H alkane stretches. The band at 3060 indicates C-H aromatic stretch; aromatics also show bands in the regions 1600-1585 and 15001400 (C-C in-ring stretch), and 900-675 (C-H out-of-plane).

Prob 21 NMR, interpreted