
(a)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Amino group reacts faster with the

Answer to Problem 27.71AP
The synthesis of given compound from the given starting material is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 1
The amine group of the
Figure 2
The complete synthesis of the given compound is shown in Figure 2.
(b)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Sodium borohydride is a strong reducing agent. The hydride ion of sodium borohydride acts as the nucleophile and gets attached to the carbonyl carbon.

Answer to Problem 27.71AP
The synthesis of given compound from the given starting material is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 3
The benzoic acid reacts with
Figure 4
The complete synthesis of the given compound is shown in Figure 4.
(c)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Aldehydes reacts with sodium cyanide to form nitrile compound. The nitrile compound reacts with ammonium chloride to form the

Answer to Problem 27.71AP
The synthesis of given compound from the given starting material is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 5
The deuteriated acetaldehyde reacts with ammonium chloride and sodium cyanide to form deuteriated
Figure 6
The synthesis of the given compound is shown in Figure 6.
(d)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Amino group reacts faster with the alkyl halides than the carboxylic group. The reaction of carboxylic acid can be performed only by protecting the amine group. Fmoc compound is used as the protecting agent for amine group. Amine and acid chloride reacts to form amide bond.

Answer to Problem 27.71AP
The synthesis of given compound from the given starting material is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 7
The cesium salt of Fmoc-proline is reacted with the resin linker. The amine is deprotecteed in pyrrolidine. Fmoc-alanine reacts with the prolin resin in presence of
Figure 8
The alanine-proline resin reacts with the Boc protected lysin to form the
Figure 9
Figure 10
The synthesis of the given compound is shown in Figure 8 and Figure 9 and Figure 10.
(e)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Aldehydes reacts with sodium cyanide to form nitrile compound. The nitrile compound reacts with ammonium chloride to form the

Answer to Problem 27.71AP
The complete synthesis of given compound is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 11
The compound
Figure 12
The synthesis of the given compound is shown in Figure 12.
(f)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
The

Answer to Problem 27.71AP
The complete synthesis of given compound is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 13
The compound cyclopentene undergo bromination reaction to form
Figure 14
The given nitrile compound upon reaction with sodium ethoxide forms anion. The formed anion reacts with
Figure 15
The complete synthesis of given compound is shown in Figure 14 and Figure 15.
(g)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
The reaction of carboxylic acid and amines to form amide is not possible. Amines are very basic so it abstracts acidic proton from the carboxylic acid. The reaction is performed in the presence of

Answer to Problem 27.71AP
The complete synthesis of given compound is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 16
The reaction between terephthalic acid and
Figure 17
The synthesis of given compound is shown in Figure 17.
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Chapter 27 Solutions
Organic Chemistry
- on x Fina X Sign X Sign x lab X Intro X Cop X chat X My x Grac x Laur x Laur x ashes x S Shox S SHE x a eve.macmillanlearning.com/ihub/assessment/f188d950-dd73-11e0-9572-0800200c9a66/d591b3f2-d5f7-4983-843c-0d00c1c0340b/f2b47861-07c4-4d1b-a1ee-e7db27d6b4ee?actualCourseld=d591b3f2-c stions estion. ct each urces. +95 Macmillan Learning Draw the product formed by the reaction of potassium t-butoxide with (15,25)-1-bromo-2-methyl-1-phenylbutane (shown). Clearly show the stereochemistry of the product. H BH (CH3)3CO-K+ +100 H3CW (CH3)3COH +85 H3CH2C +95 ossible ↓ Q Search Select Draw Templates More C H 0 bp A Erase 2Q 112 Resouarrow_forwardIdentify the structure of the PTH derivative generated after two rounds of Edman degradation.arrow_forwardUse the data below from an electron impact mass spectrum of a pure compound to deduce its structure. Draw your structure in the drawing window. Data selected from the NIST WebBook, https://webbook.nist.gov/chemistry/ m/z Relative intensity 31 0.5 30 26 29 22 28 100 27 33 26 23 15 4 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. 妊 n ? Previous Nextarrow_forward
- for this question. Write the molecular formula for a compound with the possible elements C, H, N and O that exhibits a molecular ion at M+ = 98.1106. Exact Masses of the Most Abundant Isotope of Selected Elements Isotope Natural abundance (%) Exact mass 1H 99.985 1.008 12C 98.90 12.000 14N 99.63 14.003 160 99.76 15.995 Molecular formula (In the order CHNO, with no subscripts)arrow_forwardPLEASE READ!!! I DONT WANT EXAMPLES, I DONT WANT WORDS OR PARAGRAPHS!!! PLEASE I UNDERSTAND THE BASICS BUT THIS IS AN EXCEPTION THAT EVEN THE INTERNET CANT HELP!!!! THIS IS THE THIRD TIME I'VE SENT THOSE QUESTIONS SO PLEASE DONT RESEND THE SAME STUFF, ITS NOT HELPING ME!!! I ALSO ALREADY TRIED TO DRAW THE MECHANISM MYSELF, SO IF ITS RIGHT PLEASE TELL ME OR TELL ME WHAT I HAVE TO CHANGE!!! First image: I have to SHOW (DRAWING) the mechanism (with arows and structures of molecules) NOT WORDS PLEASE! of the reaction at the bottom. Also I have to show by mecanism why the reaction wouldn't work if the alcohol was primary Second image: I have to show the mechanism (IMAGE) (with arrows and structures of the molecules) NOT WORDS PLEASE !! for the reaction on the left, where the alcohol A is added fast in one portion HOMEWORK, NOT EXAM!! ALL DETAILS ARE IN THE IMAGES PLEASE LOOK AT THE IMAGES, DONT LOOK AT THE AI GENERATED TEXT!!!arrow_forwardWrite the molecular formula for a compound with the possible elements C, H, N and O that exhibits a molecular ion at M+ = 85.0899. Exact Masses of the Most Abundant Isotope of Selected Elements Isotope Natural abundance (%) Exact mass 1H 99.985 1.008 12C 98.90 12.000 14N 99.63 14.003 160 99.76 15.995 Molecular formula (In the order CHNO, with no subscripts)arrow_forward
- Use the data below from an electron impact mass spectrum of a pure compound to deduce its structure. Draw your structure in the drawing window. Data selected from the NIST WebBook, https://webbook.nist.gov/chemistry/ m/z Relative intensity 59 3.0 58 64 43 100 15 23 • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. + n[] 85 // ? CH4 Previous Nextarrow_forwardWrite the molecular formula for a compound with the possible elements C, H, N and O that exhibits a molecular ion at M* = 128.0632. Exact Masses of the Most Abundant Isotope of Selected Elements Isotope Natural abundance (%) Exact mass 1H 99.985 12C 98.90 14N 99.63 160 99.76 Molecular formula 1.008 12.000 14.003 15.995 (In the order CHNO, with no subscripts)arrow_forwardCan I please get help with this? And can I please the lowest possible significant number?arrow_forward
- What is the molar mass of a gas that takes three times longer to effuse than helium?arrow_forwardFirst image: I have to show the mecanism (with arows and structures) of the reaction at the bottom. Also I have to show by mecanism why the reaction wouldn't work if the alcohol was primary Second image: I have to show the mecanism (with arrows and structures) for the reaction on the left, where the alcohol A is added fast in one portion its not an examarrow_forwardwhat is the skeletal structure of a tertiary alkyl fluoride with six carbon atoms and no rings.arrow_forward
