[IR - HNMR problems]

[sakaly]

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Problem1

Formula: C5H10O

IR

HNMR

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Problem2

Formula: C7H14O

HNMR

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Problem3

Formula: C4H10O

Hnmr

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Problem4

Formula: C6H14O

HNMR

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Problem5

Formula: C4H8O2

HNMR

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Problem 6

Formula: C5H10O2

HNMR

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PROBLEM 7

Formula: C8H14O3

HNMR

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PROBLEM 8

Formula: C5H10O

HNMR

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PROBLEM 9

Formula: C11H14O2

HNMR

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PROBLEM 10

Formula: C3H6O2

HNMR

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PROBLEM 11

Formula: C8H8O2

HNMR

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PROBLEM 12

Formula: C7H9N

HNMR

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PROBLEM 13

Formula: C5H13N

HNMR

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PROBLEM 14

Formula: C8H14O

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Problem 15

Formula: C4H9Br

HNMR

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PROBLEM 16

Formula: C10H14O

HNMR

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PROBLEM 17

Formula: C13H10O3

HNMR

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PROBLEM 18

Formula: C8H14

HNMR

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PROBLEM 19

Formula: C9H13N

HNMR

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PROBLEM 20

Formula: C9H10

HNMR

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Solution

Problem1:

Show Unsaturation answer: 1 degree of unsaturation.

IR The band at 1716 indicates a carbonyl, probably a ketone. The bands at 3000-2850 indicate C-H alkane
stretches.

Structure

NMR

Problem 2

Unsaturation 1 degree of unsaturation

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

Structure

NMR

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Problem3

Unsaturation 0 degrees of unsaturation.

IR The broad band at 3339 indicates an 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.

Structure

NMR

PROBLEM 4

Unsaturation 0 degrees of unsaturation.

IR 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.

Structure

NMR

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PROBLEM 5

Unsaturation 1 degree of unsaturation.

IR 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.

Structure

NMR

PROPLEM 6

Unsaturation 1 degree of unsaturation.

IR 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.

Structure

NMR

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PROBLEM 7

Unsaturation 2 degrees of unsaturation.

IR The bands at 1745 and 1716 indicate that there are two carbonyls, probably an aliphatic ester and an
aliphatic ketone. The bands at 3000-2850 indicate C-H alkane stretches.

Structure

NMR

PROBLEM 8

Unsaturation 1 degree of unsaturation.

IR The band at 1727 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.

Structure

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NMR

PROBLEM 9:

Unsaturation 5 degrees of unsaturation.

IR The band at 1603 or 1894 might indicate a carbonyl outside the normal range; the small peak around
1800 indicates it may be an aldehyde. The band at 1510 is an aromatic ring. The bands at 3000-2850
indicate C-H alkane stretches.

Structure

NMR

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PROBLEM 10

Unsaturation 1 degree of unsaturation.

IR 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.

Structure

NMR

PROBLEM 11

Unsaturation 5 degrees of unsaturation. Look for an aromatic ring, plus another pi bond or aliphatic ring.

IR The band at 1689 indicates a carbonyl, probably an acid. The broad dip at 2924 indicates the OH group
of the acid. The band at 1589 indicates an aromatic ring.

Structure

NMR

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PROBLEM 12

Unsaturation 4 degrees of unsaturation. Look for an aromatic ring, plus another pi bond or aliphatic ring.

IR The two bands at 3433 and 3354 indicate a primary amine (-NH2). 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).

Structure

NMR

PROBLEM 13

Unsaturation 0 degrees of unsaturation. No pi bonds or rings.

IR The two bands at 3388 and 3292 indicate a primary amine (-NH2). The bands at 3000-2850 indicate C-H
alkane stretches.

Structure

NMR

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PROBLEM 14

Unsaturation 2 degrees of unsaturation. Look for any 2 of pi bonds or aliphatic rings.

IR 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 weak 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).

Structure

NMR

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PROBLEM 15

Unsaturation 0 degrees of unsaturation.

IR 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.

Structure

NMR

PROBLEM 16

Unsaturation 4 degrees of unsaturation.Look for an aromatic ring.

IR The broad dip at 3250 indicates an OH group. The peak at 2963 indicates an alipahtic group. The peaks
at 1599 and 1514 indicate an aromatic ring.

Structure

NMR

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PROBLEM 17

Unsaturation 9 degrees of unsaturation. Look for 2 aromatic rings plus another pi bond or aliphatic ring.

IR 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).

Structure

NMR

PROBLEM 18

Unsaturation 2 degrees of unsaturation. Look for any 2 of pi bonds or aliphatic rings

IR 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.

Structure

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NMR

PROBLEM 19

Unsaturation4 degrees of unsaturation.Look for an aromatic ring.

IR 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 1500-1400 (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.

Structure

NMR

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PROBLEM 20

Unsaturation5 degrees of unsaturation. Look for an aromatic ring, plus another pi bond or aliphatic ring.

IR 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 1500-1400 (C-C in-ring stretch), and 900-675 (C-
H out-of-plane).

Structure

NMR

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