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Chapter 18: Q54P (page 970)

Predict the products formed when cyclopentanecarbaldehyde reacts with the following reagents.

(a) PhMgBr, then H3O+

(b) Tollens reagent

(c) semicarbazide and weak acid

(d) excess ethanol and acid

(e) propane-1-3-diol, H+

(f) zinc amalgam and dilute hydrochloric acid

Short Answer

Expert verified

The structure of cyclopentanecarbaldehyde is shown below.

cyclopentanecarbaldehyde

Step by step solution

01

Cyclopentanecarbaldehyde

The structure of cyclopentanecarbaldehyde is shown below.

cyclopentanecarbaldehyde

02

Clemmensen Reduction

Aldehydes and ketones on being reduction with zinc amalgam (Zn-Hg) and concentrated hydrochloric acid (HCL) give hydrocarbons. This is known as Clemmensen reduction.

03

Prediction of the products

(a) Cyclopentanecarbaldehyde on treatment with phenylmagnesium bromide in presence of an acidic catalyst H+ givesthe product as cyclopentyl(phenyl)methanol.

reaction a

(b) Cyclopentanecarbaldehyde on treatment with tollens reagent to givethe products as silver mirror, ammonia and cyclopentanecarboxylic acid.

reaction b

(c) Cyclopentanecarbaldehyde on treatment with hydrazinecarboxamide in presence of an weak acid givesthe product as 2-(cyclopentylmethyl)hydrazinecarboxamide.

reaction c

(d) Cyclopentanecarbaldehyde on treatment with excess ethanol and acid give sthe product as (diethoxymethyl)cyclopentane.

reaction d

(e) Cyclopentanecarbaldehyde on treatment with propane-1,3-diol in presence of an acidic catalyst H+ givesthe product as 2-cyclopentyl-1,3-dioxane.

reaction e

(f) Cyclopentanecarbaldehyde on treatment with amalgamated zinc (zinc treated with mercury) and hydrochloric aacid gives the product as methylcyclopentane

reaction f

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Most popular questions from this chapter

In the absence of water, o-phthalaldehyde has the structure shown. Its strongest IR absorption is at 1687 cm-1;the proton NMR data are shown by the structure. In the presence of water, a new compound is formed that has a strong IR absorption around 3400 cm-1and no absorption in the C=0 region. Propose a structure of X consistent with this information and suggest how X was formed.

Show how you would accomplish the following synthesis.

(a) Acetphenone鈫� acetophenone cyanohydrin

(b) Cyclopentancarbaldehyde鈫� 2-cyclopentyl-2-hydroxyacetic acid

(c) Hexan-1-ol 鈫�2-hydroxyheptanoic acid

PROBLEM 18-10

Predict the products of the following reactions:

Question. The mass spectrum of unknown compound A shows a molecular ion at m/z 116 and prominent peaks at m/z 87 and m/z 101. Its UV spectrum shows no maximum above 200 nm. The IR and NMR spectra of A follow. When A is washed with dilute aqueous acid, extracted into dichloromethane , and the solvent evaporated, it gives a product B. B shows a strong carbonyl signal at 1715 cm-1in the IR spectrum and a weak maximum at 274nm(E =16) in the UV spectrum. The mass spectrum of B shows a molecular ion of m/z 72. Determine the structures of A and B, and show the fragmentation to account for the peaks at m/z 87 and 101.

Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses alkene and triphenylphospine oxide.

  1. Show each step in the reaction of trans-2,3-epoxybutane with triphenylphospine to give but-2-ene. What is the stereochemistry of the double bond in the product?
  2. Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.
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