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The following partial IR spectra correspond to a primary amine, a secondary amine, and an alcohol. Give the functional group for each spectrum.

Short Answer

Expert verified

1st spectrum = Secondary amine

2nd structure = Primary amine

3rd structure = Alcohol

Step by step solution

01

Theory of Infrared (IR) spectrum

Infrared or IR Spectrum refers to a plot of Percentage Transmittance versus the stretching frequency of the bonds (in cm-1) . The vibrational stretching frequency for any polar bond depends on the Hooke’s Law. The equation for Hooke’s Law is as follows:

02

Detailed Explanation for answer of  the 1st Spectrum 

The IR stretching frequency value for N-H bond is sharp peak seen at around 3300 cm-1 . The general formula for secondary amine is R2NH. Since there is one N-H bond in secondary amine, sharp singlet is seen at 3300 cm-1.

Hence, the functional group is secondary amine

03

Detailed Explanation for answer of  the 2nd Spectrum 

The IR stretching frequency value for N-H bond is sharp peak seen at around 3300 cm-1. The general formula for primary amine is RNH2 . Since there are two N-H bonds in primary amine, sharp doublet is seen at 3300 cm-1.

Hence, the functional group is primary amine.

04

 Detailed Explanation for answer of  the 3rd Spectrum

The IR stretching frequency value for O-H bond is broad peak seen at around 3300 cm-1. The broad peak is seen in the spectrum at 3300 cm-1 .

Hence, the functional group is alcohol.

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Most popular questions from this chapter

Question. The carbon NMR chemical shifts of diethylmethylamine, piperidine, propan-1-ol, and propanal follow. Determine which spectrum corresponds to each structure, and show which carbon atom(s) are responsible for each absorption.

(a) 25.9, 27.8, 47.9

(b) 12.4, 41.0, 51.1

(c) 7.9, 44.7, 201.9

(d) 10.0, 25.8, 63.6

When the (R,R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the major product is the Hofman product.

  1. Draw the structure of the major (Hofman) product.
  2. Some Zaitsev product is also formed. It has the (E) configuration. When the same amine is treated with m-CPBA and heated, the Zaitsev product has the (Z) configuration. Use stereochemical drawings of the transition states to explain these observations.

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide to benzylamine

(b) 1-bromo-2-phenylethane to 3-phenylpropan-1-amine

(c) pentanoic acid to pentan-1-amine

(d) pentanoic acid to hexan-1-amine

(e) (R)-2-bromobutane to (S)-butan-2-amine

(f) (R)-2-bromobutane to (S)-2-methylbutan-1-amine

(g) hexan-2-one to 1-amino-2-methylhexan-2-ol

(A true story.) A drug user responded to an ad placed by a DEA informant in a drug-culture magazine. He later flew from Colorado to Maryland, where he bought some 1-phenyl-2-propanone (P2P) from the informant. The police waited nearly a month for the suspect to synthesize something, then obtained a search warrant, and searched the residence. They found the unopened bottle of P2P; apparently, the suspect was not a good chemist and was unable to follow the instructions the informant gave him. They also found pipes and bongs with residues of marijuana and cocaine, plus a bottle of methylamine hydrochloride, some muriatic acid (dilute HCL), zinc strips, flasks, and other equipment.

(a) Assume you are consulting for the police. Show what synthesis the suspect was prepared to carry out, to provide probable cause for the charge of attempting to manufacture a controlled substance.

(b) Assume you are a member of the jury. Would you convict the defendant of attempting to manufacture a controlled substance?

Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.

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