What carboxylic acid would be formed if the malonic ester synthesis (alkylation of diethyl malonate followed by hydrolysis with acidic workup and decarboxylation) were carried out with one equivalent of malonic ester, one equivalent of 1,5-dibromopentane, and two equivalents of hydroxide as the base

cyclohexilic acid

Explanation:

The malonic ester synthesis is often used to form different types of carboxilic acid. In this case, we have excess of base, so we can expect a ring formed in the molecule.

In the first step, the base substract the more acidic hydrogen of the ester. In the next step we have the ester reacting with the dibromopentane. Then, in the next step, the excess of base will substract again the acidic hydrogen remaining of the carbon, and then, will promove a Sn2 reaction with the bromine in the pentane (That it was previously attached to the molecule). In this step, a ring id formed. Then, the hydrolisis with acid, will form carboxilic acid in both sides of the molecule, and finally the decarboxilation in heat will separate the molecule and formed the cyclohexilic acid.

The picture below shows the mechanism

the millers tale is the answer.

most historians agree that gabriel mouton, the vicar of st. paul’s church in lyons, france, is the “founding father” of the metric system. he proposed a decimal system of measurement in 1670. mouton based it on the length of one minute of arc of a great circle of the earth (now called a nautical mile, 1852 meters). he also proposed the swing-length of a pendulum with a frequency of one beat per second as the unit of length (about 25 cm). a pendulum beating with this length would have been fairly easy to produce, thus facilitating the widespread distribution of uniform standards. over the years, his work was revised, improved, and extended by a number of french scientists.

the political sponsor of weights and measures reform in the french revolutionary national assembly was the bishop of autun, better known as talleyrand. under his auspices, the french academy appointed several committees to carry out the work of developing a usable system of weights and measures for france. one of the committees recommended a decimalized measurement system based upon a length equal to one ten-millionth of the length of a quadrant of the earth’s meridian (i.e., one ten-millionth of the distance between the equator and the north pole).